ChemWiki - User contributions [en]

It:Epibatidine

2006-11-04T14:33:52Z

Ckp05: Editing of text+reference 6

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Epibatidine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:epibatidine.gif|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 30-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 30-Oct-06 0 NONE 4
ATOM 1 Cl 0 -4.431 -0.220 0.186 0.00 0.00 Cl+0
ATOM 2 C 0 -2.719 0.001 0.004 0.00 0.00 C+0
ATOM 3 C 0 -1.877 -1.096 0.064 0.00 0.00 C+0
ATOM 4 C 0 -0.512 -0.909 -0.083 0.00 0.00 C+0
ATOM 5 C 0 -0.040 0.379 -0.286 0.00 0.00 C+0
ATOM 6 C 0 1.436 0.634 -0.452 0.00 0.00 C+0
ATOM 7 C 0 2.167 0.534 0.920 0.00 0.00 C+0
ATOM 8 N 0 2.425 -0.948 1.002 0.00 0.00 N+0
ATOM 9 C 0 3.605 1.072 0.652 0.00 0.00 C+0
ATOM 10 C 0 4.260 -0.050 -0.191 0.00 0.00 C+0
ATOM 11 C 0 3.131 -1.116 -0.319 0.00 0.00 C+0
ATOM 12 C 0 2.091 -0.488 -1.295 0.00 0.00 C+0
ATOM 13 C 0 -0.941 1.427 -0.335 0.00 0.00 C+0
ATOM 14 N 0 -2.234 1.212 -0.196 0.00 0.00 N+0
ATOM 15 H 0 -2.280 -2.086 0.224 0.00 0.00 H+0
ATOM 16 H 0 0.169 -1.746 -0.040 0.00 0.00 H+0
ATOM 17 H 0 1.607 1.609 -0.908 0.00 0.00 H+0
ATOM 18 H 0 1.641 0.973 1.767 0.00 0.00 H+0
ATOM 19 H 0 1.529 -1.404 0.912 0.00 0.00 H+0
ATOM 20 H 0 3.567 2.004 0.087 0.00 0.00 H+0
ATOM 21 H 0 4.144 1.212 1.589 0.00 0.00 H+0
ATOM 22 H 0 4.547 0.325 -1.173 0.00 0.00 H+0
ATOM 23 H 0 5.124 -0.466 0.329 0.00 0.00 H+0
ATOM 24 H 0 3.463 -2.127 -0.556 0.00 0.00 H+0
ATOM 25 H 0 1.348 -1.228 -1.592 0.00 0.00 H+0
ATOM 26 H 0 2.589 -0.070 -2.169 0.00 0.00 H+0
ATOM 27 H 0 -0.581 2.433 -0.493 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 32
CONECT 2 1 14 3 0 NONE 33
CONECT 3 2 4 15 0 NONE 34
CONECT 4 3 5 16 0 NONE 35
CONECT 5 4 6 13 0 NONE 36
CONECT 6 5 12 7 17 NONE 37
CONECT 7 6 8 9 18 NONE 38
CONECT 8 7 11 19 0 NONE 39
CONECT 9 7 10 20 21 NONE 40
CONECT 10 9 11 22 23 NONE 41
CONECT 11 10 8 12 24 NONE 42
CONECT 12 11 6 25 26 NONE 43
CONECT 13 5 14 27 0 NONE 44
CONECT 14 13 2 0 0 NONE 45
END
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+/-)-epibatidine
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 2-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C11H13ClN2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |ClC1=CC=C(C2C(N3)CCC3C2)C=N1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 208.69 g/mol
|-
| colspan="1" |Beilstein Registry number
| colspan="2" | 6139872
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" | 140111-52-0; 148152-66-3
|-
|colspan="1" |Lawson Number
| colspan="2" | 28122
|-
|colspan="1" |Appearance
| colspan="2" | White Solid
|-
|colspan="1" |Chemical Class
| colspan="2" | Alkaloid
|-
|colspan="1" |Natural isomer
| colspan="2" | (+)-epibatidine
|-
|colspan="1" |Solubility
| colspan="2" | soluble in ethanol (20mg/mL)
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |59-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
|colspan="1" |Optical Rotation of (-)-epibatidine
| colspan="2" | [α]<sub>D</sub> -5.2° (in chloroform)
|-
|colspan="1" |Optical Rotation of (+)-epibatidine
| colspan="2" | [α]<sub>D</sub> +5.4° (in chloroform)
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[nuclear magnetic resonance spectroscopy|NMR]], [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| colspan="2" |ABT-594
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Epibatidine: An Introduction==

Epibatidine was first extracted from the skin of a poisonous Ecuadorian frog, namely ''Epipedobates Tricolor'', in 1976 by John Daly. At the time it was simply called alkaloid 208/210 (its molecular mass determined via mass spectrometry). Originally he could not obtain the definitive structure of the sample he had collected (which was less than 1mg) because the analytical tools at the time did not allow him to work with such a minute quantity. He also could not extract any more from the rare frog because this particular frog species had been declared endangerd, so the sample was frozen and stored for the best part of a decade before its structure was fully declared after the development of NMR spectroscopy in 1986.<sup>1</sup>

An attempt was made to breed these unique frogs in captivity to provide a source of epibatidine. A remarkable result was deduced. The frogs bred in captivity produced no epibatidine. The researchers logically concluded that the frogs obtain this naturally scarce compound from their diets and environment.<sup>1</sup>

Daly obtained evidence that this compound was a potent analgesic. In the hot plate assay and Straub-tail assays respectively it was found to be 200-500 times more potent than morphine.<sup>5</sup> Moreover, epibatidine was found to have negligible (1/8000) affinity for opiate receptors (it is not an opioid like morphine). Daly showed that naloxone (an opioid antagonist) did not block the action of epibatidine. The significance of this discovery is that it provides strong evidence that epibatidine is not addictive, unlike morphine.<sup>1</sup>

It was observed that epibatidine has a similar structure to nicotine. Soon after it was found that epibatidine binds to nicotinic acetylcholine receptors.<sup>1</sup> This provided a solution to its analgesic powers. However, the potential of epibatidine as an analgesic was ended when it was found that it binds very strongly to the neuromuscular receptor in which acetyl choline regulates muscle contraction and relaxation. As a result epibatidine causes paralysis and can be fatal if the muscles in conjunction with the respiratory system become depressed.<sup>1</sup>

===ABT-594 – An Analogue of epibatidine: a possible future analgesic?===

Epibatidine was determined useless as an analgesic due to its toxicity. Nonetheless, researchers were excited by the possibility of developing an analgesic through epibatidine-like derivatives that did not render toxicity.

Among the many tested, ABT-594 is the most famous example and was found to be 50 times more potent that morphine as well as not possessing its addictive nature. More importantly it also demonstrated no cases of paralysis or depression of muscle action during clinical trials. This drug has undergone Phase I trials with success and has recently completed its latest trial set, Phase II, although the results of the latter trial are yet to be published.<sup>1</sup>

==Synthesis<sup>1+6</sup>==

There are two optical isomers of epibatidine. The (+)-epibatidine isomer is the naturally occurring isomer that is found on the skin of the ''Epipedobates Tricolor frog''. However, the (-)-epibatidine isomer also possesses the analgesic properties so sought after, so a racemic mixture of the two isomers would be just as effective as a painkiller.

There have been many different synthetic routes to attempt to produce epibatidine in the past, as it has been such a sought after compound for research. A variety of synthetic strategies have also been employed.

===The Corey Synthesis===

This synthesis was developed in 1993, just one year after Daly had released the structure of epibatidine. It is stereospecific, in that the endo-form is not produced. The enantiomers of epibatidine that are produced as a racemic mixture from this synthesis can be separated by liquid chromatography, due to their different eluting times, if desired.

[[Image:corey_steps_1_2.gif|thumb|left|200|Corey Synthesis: Initial Stages]]

The first step involves converting the starting material to the (Z)-stereoisomer of the α,β-unsaturated ester with the aid of the Still-Gennari reagent. This mechanism is stereospecific because the transition state corresponding to that of the (Z)-stereoisomer is less hindered and therefore the product formed via this route is more thermodynamically stable. The second step involves a simple thermal Diels-Alder reaction, performed at 190°C.

[[Image:corey_steps_3_4_5.gif|thumb|left|200|Corey Syntheis: Intermediate Stages]]

In Step 3 saponification of the ester forms the corresponding carboxylic acid, which is in turn transformed into an acyl azide (Step 4). The removal of the TMS protecting group is then performed via a carbamate cleavage to give the corresponding primary amine. This amine then undergoes an acylation reaction with tetrafluroacetic acid, producing Compound 7.

[[Image:corey_steps_6_7_8_9.gif|thumb|left|200|Corey Synthesis: Final Stages]]

The production of compound 8 requires the key stereospecific halogenation, in the presence of bromine and a source of the bromide ion. Stereospecificity is due to the kinetically favoured attack of the bromide ion ''cis'' to the NHCOCF<sub>3</sub> group. An excess source of bromide ion (10 mole equivalents) is fundamental to the stereospecific nature for this reaction, as its presence directly stabilises the ''cis''-bromium ion. The formation of the bicyclic ring can then proceed under basic conditions via nucleophilic attack (Step 7). Debromination and deacetylation in Steps 8 and 9 respectively lead to the desired product.

Each step in this synthesis is performed with a fairly high yield culminating in an overall yield of 40%.

===Huang and Shen===

This synthetic route (published in 1993 as well) is perhaps conceptually simpler than the Corey Synthesis, although it produces a lower yield, 25% of the epibatidine. Another problem with this synthesis is that it also produces the endo-isomer of epibatidine (with a yield of 28%), although silica gel chromatography can used to separate this isomer from the desired exo-isomer.

The first step involves a Diels-Alder reaction involving the two starting materials: N-carbomethoxypyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene. The two unwanted double bonds were then reduced by first sodium amalgam and then a Platinum catalyst and hydrogen. The final step involves the removal of the N-carbomethoxy protecting group to reveal the desired product.

[[Image:huang_scheme.gif|thumb|left|200|Huang and Shen Synthesis]]

==References==

1. Jenny Pan, 2004, http://www.chemsoc.org/ExemplarChem/entries/2004/icl_Pan/page2.html

2. The Science Center, 2004, http://www.science-education.org/classroom_activities/chlorine_compound/epibatidine.html

3. Matthew J. Dowd, Department of Medicinal Chemistry of
Virginia Commonwealth University, http://www.phc.vcu.edu/Feature/oldfeature/epi/

4 Chris A Broka, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''20''', 3251-3254, {{DOI|10.1016/S0040-4039(00)73674-4}}

5. Dao Fei Huang, T. Y. Shen, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''28''', 4477-4480, {{DOI|10.1016/0040-4039(93)88063-O}}

6. E. J. Corey, Teck-Peng Loh, Sidduri AchyuthaRao, Donnette C Daley, Sepehr Sarshar, ''J Org. Chem'', 1993, '''58''', 5600-5602, {{DOI|10.1021/jo00073a013}}

It:Epibatidine

2006-11-04T13:58:57Z

Ckp05: text edit - Greek letters

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Epibatidine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:epibatidine.gif|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 30-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 30-Oct-06 0 NONE 4
ATOM 1 Cl 0 -4.431 -0.220 0.186 0.00 0.00 Cl+0
ATOM 2 C 0 -2.719 0.001 0.004 0.00 0.00 C+0
ATOM 3 C 0 -1.877 -1.096 0.064 0.00 0.00 C+0
ATOM 4 C 0 -0.512 -0.909 -0.083 0.00 0.00 C+0
ATOM 5 C 0 -0.040 0.379 -0.286 0.00 0.00 C+0
ATOM 6 C 0 1.436 0.634 -0.452 0.00 0.00 C+0
ATOM 7 C 0 2.167 0.534 0.920 0.00 0.00 C+0
ATOM 8 N 0 2.425 -0.948 1.002 0.00 0.00 N+0
ATOM 9 C 0 3.605 1.072 0.652 0.00 0.00 C+0
ATOM 10 C 0 4.260 -0.050 -0.191 0.00 0.00 C+0
ATOM 11 C 0 3.131 -1.116 -0.319 0.00 0.00 C+0
ATOM 12 C 0 2.091 -0.488 -1.295 0.00 0.00 C+0
ATOM 13 C 0 -0.941 1.427 -0.335 0.00 0.00 C+0
ATOM 14 N 0 -2.234 1.212 -0.196 0.00 0.00 N+0
ATOM 15 H 0 -2.280 -2.086 0.224 0.00 0.00 H+0
ATOM 16 H 0 0.169 -1.746 -0.040 0.00 0.00 H+0
ATOM 17 H 0 1.607 1.609 -0.908 0.00 0.00 H+0
ATOM 18 H 0 1.641 0.973 1.767 0.00 0.00 H+0
ATOM 19 H 0 1.529 -1.404 0.912 0.00 0.00 H+0
ATOM 20 H 0 3.567 2.004 0.087 0.00 0.00 H+0
ATOM 21 H 0 4.144 1.212 1.589 0.00 0.00 H+0
ATOM 22 H 0 4.547 0.325 -1.173 0.00 0.00 H+0
ATOM 23 H 0 5.124 -0.466 0.329 0.00 0.00 H+0
ATOM 24 H 0 3.463 -2.127 -0.556 0.00 0.00 H+0
ATOM 25 H 0 1.348 -1.228 -1.592 0.00 0.00 H+0
ATOM 26 H 0 2.589 -0.070 -2.169 0.00 0.00 H+0
ATOM 27 H 0 -0.581 2.433 -0.493 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 32
CONECT 2 1 14 3 0 NONE 33
CONECT 3 2 4 15 0 NONE 34
CONECT 4 3 5 16 0 NONE 35
CONECT 5 4 6 13 0 NONE 36
CONECT 6 5 12 7 17 NONE 37
CONECT 7 6 8 9 18 NONE 38
CONECT 8 7 11 19 0 NONE 39
CONECT 9 7 10 20 21 NONE 40
CONECT 10 9 11 22 23 NONE 41
CONECT 11 10 8 12 24 NONE 42
CONECT 12 11 6 25 26 NONE 43
CONECT 13 5 14 27 0 NONE 44
CONECT 14 13 2 0 0 NONE 45
END
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+/-)-epibatidine
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 2-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C11H13ClN2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |ClC1=CC=C(C2C(N3)CCC3C2)C=N1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 208.69 g/mol
|-
| colspan="1" |Beilstein Registry number
| colspan="2" | 6139872
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" | 140111-52-0; 148152-66-3
|-
|colspan="1" |Lawson Number
| colspan="2" | 28122
|-
|colspan="1" |Appearance
| colspan="2" | White Solid
|-
|colspan="1" |Chemical Class
| colspan="2" | Alkaloid
|-
|colspan="1" |Natural isomer
| colspan="2" | (+)-epibatidine
|-
|colspan="1" |Solubility
| colspan="2" | soluble in ethanol (20mg/mL)
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |59-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
|colspan="1" |Optical Rotation of (-)-epibatidine
| colspan="2" | [α]<sub>D</sub> -5.2° (in chloroform)
|-
|colspan="1" |Optical Rotation of (+)-epibatidine
| colspan="2" | [α]<sub>D</sub> +5.4° (in chloroform)
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[nuclear magnetic resonance spectroscopy|NMR]], [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| colspan="2" |ABT-594
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Epibatidine: An Introduction==

Epibatidine was first extracted from the skin of a poisonous Ecuadorian frog, namely ''Epipedobates Tricolor'', in 1976 by John Daly. At the time it was simply called alkaloid 208/210 (its molecular mass determined via mass spectrometry). Originally he could not obtain the definitive structure of the sample he had collected (which was less than 1mg) because the analytical tools at the time did not allow him to work with such a minute quantity. He also could not extract any more from the rare frog because this particular frog species had been declared endangerd, so the sample was frozen and stored for the best part of a decade before its structure was fully declared after the development of NMR spectroscopy in 1986.<sup>1</sup>

An attempt was made to breed these unique frogs in captivity to provide a source of epibatidine. A remarkable result was deduced. The frogs bred in captivity produced no epibatidine. The researchers logically concluded that the frogs obtain this naturally scarce compound from their diets and environment.<sup>1</sup>

Daly obtained evidence that this compound was a potent analgesic. In the hot plate assay and Straub-tail assays respectively it was found to be 200-500 times more potent than morphine.<sup>5</sup> Moreover, epibatidine was found to have negligible (1/8000) affinity for opiate receptors (it is not an opioid like morphine). Daly showed that naloxone (an opioid antagonist) did not block the action of epibatidine. The significance of this discovery is that it provides strong evidence that epibatidine is not addictive, unlike morphine.<sup>1</sup>

It was observed that epibatidine has a similar structure to nicotine. Soon after it was found that epibatidine binds to nicotinic acetylcholine receptors.<sup>1</sup> This provided a solution to its analgesic powers. However, the potential of epibatidine as an analgesic was ended when it was found that it binds very strongly to the neuromuscular receptor in which acetyl choline regulates muscle contraction and relaxation. As a result epibatidine causes paralysis and can be fatal if the muscles in conjunction with the respiratory system become depressed.<sup>1</sup>

===ABT-594 – An Analogue of epibatidine: a possible future analgesic?===

Epibatidine was determined useless as an analgesic due to its toxicity. Nonetheless, researchers were excited by the possibility of developing an analgesic through epibatidine-like derivatives that did not render toxicity.

Among the many tested, ABT-594 is the most famous example and was found to be 50 times more potent that morphine as well as not possessing its addictive nature. More importantly it also demonstrated no cases of paralysis or depression of muscle action during clinical trials. This drug has undergone Phase I trials with success and has recently completed its latest trial set, Phase II, although the results of the latter trial are yet to be published.<sup>1</sup>

==Synthesis<sup>1</sup>==

There are two optical isomers of epibatidine. The (+)-epibatidine isomer is the naturally occurring isomer that is found on the skin of the ''Epipedobates Tricolor frog''. However, the (-)-epibatidine isomer also possesses the analgesic properties so sought after, so a racemic mixture of the two isomers would be just as effective as a painkiller.

There have been many different synthetic routes to attempt to produce epibatidine in the past, as it has been such a sought after compound for research. A variety of synthetic strategies have also been employed.

===The Corey Synthesis===

This synthesis was developed in 1993, just one year after Daly had released the structure of epibatidine. It is stereospecific, in that the endo-form is not produced. The enantiomers of epibatidine that are produced as a racemic mixture from this synthesis can be separated by liquid chromatography, due to their different eluting times, if desired.

[[Image:corey_steps_1_2.gif|thumb|left|200|Corey Synthesis: Initial Stages]]

The first step involves converting the starting material to the (Z)-stereoisomer of the α,β-unsaturated ester. This mechanism is stereospecific because the transition state corresponding to that of the (Z)-stereoisomer is less hindered and therefore the product formed via this route is more thermodynamically stable. The second step involves a simple Diels-Alder reaction.

[[Image:corey_steps_3_4_5.gif|thumb|left|200|Corey Syntheis: Intermediate Stages]]

In Step 3 saponification of the ester forms a carboxylic acid, which is in turn transformed into an acyl azide (Step 4). The removal of the TMS protecting group is then performed and acylation with tetrafluroacetic acid produces Compound 7.

[[Image:corey_steps_6_7_8_9.gif|thumb|left|200|Corey Synthesis: Final Stages]]

The production of compound 8 requires the key stereospecific halogenation, in the presence of bromine and a source of the bromide ion. Stereospecificity is due to the kinetically favoured attack of the bromide ion ''cis'' to the NHCOCF<sub>3</sub> group. An excess source of bromide ion (10 mole equivalents) is fundamental to the stereospecific nature for this reaction, as its presence directly stabilises the ''cis''-bromium ion. The formation of the bicyclic ring can then proceed under basic conditions via nucleophilic attack (Step 7). Debromination and deacetylation in Steps 8 and 9 respectively lead to the desired product.

Each step in this synthesis is performed with a fairly high yield culminating in an overall yield of 40%.

===Huang and Shen===

This synthetic route (published in 1993 as well) is perhaps conceptually simpler than the Corey Synthesis, although it produces a lower yield, 25% of the epibatidine. Another problem with this synthesis is that it also produces the endo-isomer of epibatidine (with a yield of 28%), although silica gel chromatography can used to separate this isomer from the desired exo-isomer.

The first step involves a Diels-Alder reaction involving the two starting materials: N-carbomethoxypyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene. The two unwanted double bonds were then reduced by first sodium amalgam and then a Platinum catalyst and hydrogen. The final step involves the removal of the N-carbomethoxy protecting group to reveal the desired product.

[[Image:huang_scheme.gif|thumb|left|200|Huang and Shen Synthesis]]

==References==

1. Jenny Pan, 2004, http://www.chemsoc.org/ExemplarChem/entries/2004/icl_Pan/page2.html

2. The Science Center, 2004, http://www.science-education.org/classroom_activities/chlorine_compound/epibatidine.html

3. Matthew J. Dowd, Department of Medicinal Chemistry of
Virginia Commonwealth University, http://www.phc.vcu.edu/Feature/oldfeature/epi/

4 Chris A Broka, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''20''', 3251-3254, {{DOI|10.1016/S0040-4039(00)73674-4}}

5. Dao Fei Huang, T. Y. Shen, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''28''', 4477-4480, {{DOI|10.1016/0040-4039(93)88063-O}}

It:Epibatidine

2006-11-04T13:55:52Z

Ckp05: Text Editing (changing relevant text to Italic, adding subscripts/superscripts etc

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Epibatidine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:epibatidine.gif|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 30-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 30-Oct-06 0 NONE 4
ATOM 1 Cl 0 -4.431 -0.220 0.186 0.00 0.00 Cl+0
ATOM 2 C 0 -2.719 0.001 0.004 0.00 0.00 C+0
ATOM 3 C 0 -1.877 -1.096 0.064 0.00 0.00 C+0
ATOM 4 C 0 -0.512 -0.909 -0.083 0.00 0.00 C+0
ATOM 5 C 0 -0.040 0.379 -0.286 0.00 0.00 C+0
ATOM 6 C 0 1.436 0.634 -0.452 0.00 0.00 C+0
ATOM 7 C 0 2.167 0.534 0.920 0.00 0.00 C+0
ATOM 8 N 0 2.425 -0.948 1.002 0.00 0.00 N+0
ATOM 9 C 0 3.605 1.072 0.652 0.00 0.00 C+0
ATOM 10 C 0 4.260 -0.050 -0.191 0.00 0.00 C+0
ATOM 11 C 0 3.131 -1.116 -0.319 0.00 0.00 C+0
ATOM 12 C 0 2.091 -0.488 -1.295 0.00 0.00 C+0
ATOM 13 C 0 -0.941 1.427 -0.335 0.00 0.00 C+0
ATOM 14 N 0 -2.234 1.212 -0.196 0.00 0.00 N+0
ATOM 15 H 0 -2.280 -2.086 0.224 0.00 0.00 H+0
ATOM 16 H 0 0.169 -1.746 -0.040 0.00 0.00 H+0
ATOM 17 H 0 1.607 1.609 -0.908 0.00 0.00 H+0
ATOM 18 H 0 1.641 0.973 1.767 0.00 0.00 H+0
ATOM 19 H 0 1.529 -1.404 0.912 0.00 0.00 H+0
ATOM 20 H 0 3.567 2.004 0.087 0.00 0.00 H+0
ATOM 21 H 0 4.144 1.212 1.589 0.00 0.00 H+0
ATOM 22 H 0 4.547 0.325 -1.173 0.00 0.00 H+0
ATOM 23 H 0 5.124 -0.466 0.329 0.00 0.00 H+0
ATOM 24 H 0 3.463 -2.127 -0.556 0.00 0.00 H+0
ATOM 25 H 0 1.348 -1.228 -1.592 0.00 0.00 H+0
ATOM 26 H 0 2.589 -0.070 -2.169 0.00 0.00 H+0
ATOM 27 H 0 -0.581 2.433 -0.493 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 32
CONECT 2 1 14 3 0 NONE 33
CONECT 3 2 4 15 0 NONE 34
CONECT 4 3 5 16 0 NONE 35
CONECT 5 4 6 13 0 NONE 36
CONECT 6 5 12 7 17 NONE 37
CONECT 7 6 8 9 18 NONE 38
CONECT 8 7 11 19 0 NONE 39
CONECT 9 7 10 20 21 NONE 40
CONECT 10 9 11 22 23 NONE 41
CONECT 11 10 8 12 24 NONE 42
CONECT 12 11 6 25 26 NONE 43
CONECT 13 5 14 27 0 NONE 44
CONECT 14 13 2 0 0 NONE 45
END
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+/-)-epibatidine
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 2-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C11H13ClN2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |ClC1=CC=C(C2C(N3)CCC3C2)C=N1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 208.69 g/mol
|-
| colspan="1" |Beilstein Registry number
| colspan="2" | 6139872
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" | 140111-52-0; 148152-66-3
|-
|colspan="1" |Lawson Number
| colspan="2" | 28122
|-
|colspan="1" |Appearance
| colspan="2" | White Solid
|-
|colspan="1" |Chemical Class
| colspan="2" | Alkaloid
|-
|colspan="1" |Natural isomer
| colspan="2" | (+)-epibatidine
|-
|colspan="1" |Solubility
| colspan="2" | soluble in ethanol (20mg/mL)
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |59-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
|colspan="1" |Optical Rotation of (-)-epibatidine
| colspan="2" | [α]<sub>D</sub> -5.2° (in chloroform)
|-
|colspan="1" |Optical Rotation of (+)-epibatidine
| colspan="2" | [α]<sub>D</sub> +5.4° (in chloroform)
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[nuclear magnetic resonance spectroscopy|NMR]], [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| colspan="2" |ABT-594
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Epibatidine: An Introduction==

Epibatidine was first extracted from the skin of a poisonous Ecuadorian frog, namely ''Epipedobates Tricolor'', in 1976 by John Daly. At the time it was simply called alkaloid 208/210 (its molecular mass determined via mass spectrometry). Originally he could not obtain the definitive structure of the sample he had collected (which was less than 1mg) because the analytical tools at the time did not allow him to work with such a minute quantity. He also could not extract any more from the rare frog because this particular frog species had been declared endangerd, so the sample was frozen and stored for the best part of a decade before its structure was fully declared after the development of NMR spectroscopy in 1986.<sup>1</sup>

An attempt was made to breed these unique frogs in captivity to provide a source of epibatidine. A remarkable result was deduced. The frogs bred in captivity produced no epibatidine. The researchers logically concluded that the frogs obtain this naturally scarce compound from their diets and environment.<sup>1</sup>

Daly obtained evidence that this compound was a potent analgesic. In the hot plate assay and Straub-tail assays respectively it was found to be 200-500 times more potent than morphine.<sup>5</sup> Moreover, epibatidine was found to have negligible (1/8000) affinity for opiate receptors (it is not an opioid like morphine). Daly showed that naloxone (an opioid antagonist) did not block the action of epibatidine. The significance of this discovery is that it provides strong evidence that epibatidine is not addictive, unlike morphine.<sup>1</sup>

It was observed that epibatidine has a similar structure to nicotine. Soon after it was found that epibatidine binds to nicotinic acetylcholine receptors.<sup>1</sup> This provided a solution to its analgesic powers. However, the potential of epibatidine as an analgesic was ended when it was found that it binds very strongly to the neuromuscular receptor in which acetyl choline regulates muscle contraction and relaxation. As a result epibatidine causes paralysis and can be fatal if the muscles in conjunction with the respiratory system become depressed.<sup>1</sup>

===ABT-594 – An Analogue of epibatidine: a possible future analgesic?===

Epibatidine was determined useless as an analgesic due to its toxicity. Nonetheless, researchers were excited by the possibility of developing an analgesic through epibatidine-like derivatives that did not render toxicity.

Among the many tested, ABT-594 is the most famous example and was found to be 50 times more potent that morphine as well as not possessing its addictive nature. More importantly it also demonstrated no cases of paralysis or depression of muscle action during clinical trials. This drug has undergone Phase I trials with success and has recently completed its latest trial set, Phase II, although the results of the latter trial are yet to be published.<sup>1</sup>

==Synthesis<sup>1</sup>==

There are two optical isomers of epibatidine. The (+)-epibatidine isomer is the naturally occurring isomer that is found on the skin of the ''Epipedobates Tricolor frog''. However, the (-)-epibatidine isomer also possesses the analgesic properties so sought after, so a racemic mixture of the two isomers would be just as effective as a painkiller.

There have been many different synthetic routes to attempt to produce epibatidine in the past, as it has been such a sought after compound for research. A variety of synthetic strategies have also been employed.

===The Corey Synthesis===

This synthesis was developed in 1993, just one year after Daly had released the structure of epibatidine. It is stereospecific, in that the endo-form is not produced. The enantiomers of epibatidine that are produced as a racemic mixture from this synthesis can be separated by liquid chromatography, due to their different eluting times, if desired.

[[Image:corey_steps_1_2.gif|thumb|left|200|Corey Synthesis: Initial Stages]]

The first step involves converting the starting material to the (Z)-stereoisomer of the alpha,Beta-unsaturated ester. This mechanism is stereospecific because the transition state corresponding to that of the (Z)-stereoisomer is less hindered and therefore the product formed via this route is more thermodynamically stable. The second step involves a simple Diels-Alder reaction.

[[Image:corey_steps_3_4_5.gif|thumb|left|200|Corey Syntheis: Intermediate Stages]]

In Step 3 saponification of the ester forms a carboxylic acid, which is in turn transformed into an acyl azide (Step 4). The removal of the TMS protecting group is then performed and acylation with tetrafluroacetic acid produces Compound 7.

[[Image:corey_steps_6_7_8_9.gif|thumb|left|200|Corey Synthesis: Final Stages]]

The production of compound 8 requires the key stereospecific halogenation, in the presence of bromine and a source of the bromide ion. Stereospecificity is due to the kinetically favoured attack of the bromide ion ''cis'' to the NHCOCF<sub>3</sub> group. An excess source of bromide ion (10 mole equivalents) is fundamental to the stereospecific nature for this reaction, as its presence directly stabilises the ''cis''-bromium ion. The formation of the bicyclic ring can then proceed under basic conditions via nucleophilic attack (Step 7). Debromination and deacetylation in Steps 8 and 9 respectively lead to the desired product.

Each step in this synthesis is performed with a fairly high yield culminating in an overall yield of 40%.

===Huang and Shen===

This synthetic route (published in 1993 as well) is perhaps conceptually simpler than the Corey Synthesis, although it produces a lower yield, 25% of the epibatidine. Another problem with this synthesis is that it also produces the endo-isomer of epibatidine (with a yield of 28%), although silica gel chromatography can used to separate this isomer from the desired exo-isomer.

The first step involves a Diels-Alder reaction involving the two starting materials: N-carbomethoxypyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene. The two unwanted double bonds were then reduced by first sodium amalgam and then a Platinum catalyst and hydrogen. The final step involves the removal of the N-carbomethoxy protecting group to reveal the desired product.

[[Image:huang_scheme.gif|thumb|left|200|Huang and Shen Synthesis]]

==References==

1. Jenny Pan, 2004, http://www.chemsoc.org/ExemplarChem/entries/2004/icl_Pan/page2.html

2. The Science Center, 2004, http://www.science-education.org/classroom_activities/chlorine_compound/epibatidine.html

3. Matthew J. Dowd, Department of Medicinal Chemistry of
Virginia Commonwealth University, http://www.phc.vcu.edu/Feature/oldfeature/epi/

4 Chris A Broka, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''20''', 3251-3254, {{DOI|10.1016/S0040-4039(00)73674-4}}

5. Dao Fei Huang, T. Y. Shen, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''28''', 4477-4480, {{DOI|10.1016/0040-4039(93)88063-O}}

It:Epibatidine

2006-11-04T13:26:37Z

Ckp05: Addition of text for Intro+Synthesis+diagrams of sythesis+references+DOI links

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Epibatidine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:epibatidine.gif|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 30-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 30-Oct-06 0 NONE 4
ATOM 1 Cl 0 -4.431 -0.220 0.186 0.00 0.00 Cl+0
ATOM 2 C 0 -2.719 0.001 0.004 0.00 0.00 C+0
ATOM 3 C 0 -1.877 -1.096 0.064 0.00 0.00 C+0
ATOM 4 C 0 -0.512 -0.909 -0.083 0.00 0.00 C+0
ATOM 5 C 0 -0.040 0.379 -0.286 0.00 0.00 C+0
ATOM 6 C 0 1.436 0.634 -0.452 0.00 0.00 C+0
ATOM 7 C 0 2.167 0.534 0.920 0.00 0.00 C+0
ATOM 8 N 0 2.425 -0.948 1.002 0.00 0.00 N+0
ATOM 9 C 0 3.605 1.072 0.652 0.00 0.00 C+0
ATOM 10 C 0 4.260 -0.050 -0.191 0.00 0.00 C+0
ATOM 11 C 0 3.131 -1.116 -0.319 0.00 0.00 C+0
ATOM 12 C 0 2.091 -0.488 -1.295 0.00 0.00 C+0
ATOM 13 C 0 -0.941 1.427 -0.335 0.00 0.00 C+0
ATOM 14 N 0 -2.234 1.212 -0.196 0.00 0.00 N+0
ATOM 15 H 0 -2.280 -2.086 0.224 0.00 0.00 H+0
ATOM 16 H 0 0.169 -1.746 -0.040 0.00 0.00 H+0
ATOM 17 H 0 1.607 1.609 -0.908 0.00 0.00 H+0
ATOM 18 H 0 1.641 0.973 1.767 0.00 0.00 H+0
ATOM 19 H 0 1.529 -1.404 0.912 0.00 0.00 H+0
ATOM 20 H 0 3.567 2.004 0.087 0.00 0.00 H+0
ATOM 21 H 0 4.144 1.212 1.589 0.00 0.00 H+0
ATOM 22 H 0 4.547 0.325 -1.173 0.00 0.00 H+0
ATOM 23 H 0 5.124 -0.466 0.329 0.00 0.00 H+0
ATOM 24 H 0 3.463 -2.127 -0.556 0.00 0.00 H+0
ATOM 25 H 0 1.348 -1.228 -1.592 0.00 0.00 H+0
ATOM 26 H 0 2.589 -0.070 -2.169 0.00 0.00 H+0
ATOM 27 H 0 -0.581 2.433 -0.493 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 32
CONECT 2 1 14 3 0 NONE 33
CONECT 3 2 4 15 0 NONE 34
CONECT 4 3 5 16 0 NONE 35
CONECT 5 4 6 13 0 NONE 36
CONECT 6 5 12 7 17 NONE 37
CONECT 7 6 8 9 18 NONE 38
CONECT 8 7 11 19 0 NONE 39
CONECT 9 7 10 20 21 NONE 40
CONECT 10 9 11 22 23 NONE 41
CONECT 11 10 8 12 24 NONE 42
CONECT 12 11 6 25 26 NONE 43
CONECT 13 5 14 27 0 NONE 44
CONECT 14 13 2 0 0 NONE 45
END
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+/-)-epibatidine
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 2-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]heptane
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C11H13ClN2
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |ClC1=CC=C(C2C(N3)CCC3C2)C=N1
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 208.69 g/mol
|-
| colspan="1" |Beilstein Registry number
| colspan="2" | 6139872
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" | 140111-52-0; 148152-66-3
|-
|colspan="1" |Lawson Number
| colspan="2" | 28122
|-
|colspan="1" |Appearance
| colspan="2" | White Solid
|-
|colspan="1" |Chemical Class
| colspan="2" | Alkaloid
|-
|colspan="1" |Natural isomer
| colspan="2" | (+)-epibatidine
|-
|colspan="1" |Solubility
| colspan="2" | soluble in ethanol (20mg/mL)
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |59-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
|colspan="1" |Optical Rotation of (-)-epibatidine
| colspan="2" | [α]<sub>D</sub> -5.2° (in chloroform)
|-
|colspan="1" |Optical Rotation of (+)-epibatidine
| colspan="2" | [α]<sub>D</sub> +5.4° (in chloroform)
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[nuclear magnetic resonance spectroscopy|NMR]], [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| colspan="2" |ABT-594
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Epibatidine: An Introduction==

Epibatidine was first extracted from the skin of a poisonous Ecuadorian frog, namely ''Epipedobates Tricolor'', in 1976 by John Daly. At the time it was simply called alkaloid 208/210 (its molecular mass determined via mass spectrometry). Originally he could not obtain the definitive structure of the sample he had collected (which was less than 1mg) because the analytical tools at the time did not allow him to work with such a minute quantity. He also could not extract any more from the rare frog because this particular frog species had been declared endangerd, so the sample was frozen and stored for the best part of a decade before its structure was fully declared after the development of NMR spectroscopy in 1986.<sup>1</sup>

An attempt was made to breed these unique frogs in captivity to provide a source of epibatidine. A remarkable result was deduced. The frogs bred in captivity produced no epibatidine. The researchers logically concluded that the frogs obtain this naturally scarce compound from their diets and environment.<sup>1</sup>

Daly obtained evidence that this compound was a potent analgesic. In the hot plate assay and Straub-tail assays respectively it was found to be 200-500 times more potent than morphine.<sup>5</sup> Moreover, epibatidine was found to have negligible (1/8000) affinity for opiate receptors (it is not an opioid like morphine). Daly showed that naloxone (an opioid antagonist) did not block the action of epibatidine. The significance of this discovery is that it provides strong evidence that epibatidine is not addictive, unlike morphine.<sup>1</sup>

It was observed that epibatidine has a similar structure to nicotine. Soon after it was found that epibatidine binds to nicotinic acetylcholine receptors.<sup>1</sup> This provided a solution to its analgesic powers. However, the potential of epibatidine as an analgesic was ended when it was found that it binds very strongly to the neuromuscular receptor in which acetyl choline regulates muscle contraction and relaxation. As a result epibatidine causes paralysis and can be fatal if the muscles in conjunction with the respiratory system become depressed.<sup>1</sup>

===ABT-594 – An Analogue of epibatidine: a possible future analgesic?===

Epibatidine was determined useless as an analgesic due to its toxicity. Nonetheless, researchers were excited by the possibility of developing an analgesic through epibatidine-like derivatives that did not render toxicity.

Among the many tested, ABT-594 is the most famous example and was found to be 50 times more potent that morphine as well as not possessing its addictive nature. More importantly it also demonstrated no cases of paralysis or depression of muscle action during clinical trials. This drug has undergone Phase I trials with success and has recently completed its latest trial set, Phase II, although the results of the latter trial are yet to be published.<sup>1</sup>

==Synthesis<sup>1</sup>==

There are two optical isomers of epibatidine. The (+)-epibatidine isomer is the naturally occurring isomer that is found on the skin of the Epipedobates Tricolor frog. However, the (-)-epibatidine isomer also possesses the analgesic properties so sought after, so a racemic mixture of the two isomers would be just as effective as a painkiller.

There have been many different synthetic routes to attempt to produce epibatidine in the past, as it has been such a sought after compound for research. A variety of synthetic strategies have also been employed.

===The Corey Synthesis===

This synthesis was developed in 1993, just one year after Daly had released the structure of epibatidine. It is stereospecific, in that the endo-form is not produced. The enantiomers of epibatidine that are produced as a racemic mixture from this synthesis can be separated by liquid chromatography, due to their different eluting times, if desired.

[[Image:corey_steps_1_2.gif|thumb|left|200|Corey Synthesis: Initial Stages]]

The first step involves converting the starting material to the (Z)-stereoisomer of the alpha,Beta-unsaturated ester. This mechanism is stereospecific because the transition state corresponding to that of the (Z)-stereoisomer is less hindered and therefore the product formed via this route is more thermodynamically stable. The second step involves a simple Diels-Alder reaction.

[[Image:corey_steps_3_4_5.gif|thumb|left|200|Corey Syntheis: Intermediate Stages]]

In Step 3 saponification of the ester forms a carboxylic acid, which is in turn transformed into an acyl azide (Step 4). The removal of the TMS protecting group is then performed and acylation with tetrafluroacetic acid produces Compound 7.

[[Image:corey_steps_6_7_8_9.gif|thumb|left|200|Corey Synthesis: Final Stages]]

The production of compound 8 requires the key stereospecific halogenation, in the presence of bromine and a source of the bromide ion. Stereospecificity is due to the kinetically favoured attack of the bromide ion ‘’cis’’ to the NHCOCF3 group. An excess source of bromide ion (10 mole equivalents) is fundamental to the stereospecific nature for this reaction, as its presence directly stabilises the ‘’cis’’-bromium ion. The formation of the bicyclic ring can then proceed under basic conditions via nucleophilic attack (Step 7). Debromination and deacetylation in Steps 8 and 9 respectively lead to the desired product.

Each step in this synthesis is performed with a fairly high yield culminating in an overall yield of 40%.

===Huang and Shen===

This synthetic route (published in 1993 as well) is perhaps conceptually simpler than the Corey Synthesis, although it produces a lower yield, 25% of the epibatidine. Another problem with this synthesis is that it also produces the endo-isomer of epibatidine (with a yield of 28%), although silica gel chromatography can used to separate this isomer from the desired exo-isomer.

The first step involves a Diels-Alder reaction involving the two starting materials: N-carbomethoxypyrrole and phenylsulfonyl 6-chloro-3-pyridyl acetylene. The two unwanted double bonds were then reduced by first sodium amalgam and then a Platinum catalyst and hydrogen. The final step involves the removal of the N-carbomethoxy protecting group to reveal the desired product.

[[Image:huang_scheme.gif|thumb|left|200|Huang and Shen Synthesis]]

==References==

1. Jenny Pan, 2004, http://www.chemsoc.org/ExemplarChem/entries/2004/icl_Pan/page2.html

2. The Science Center, 2004, http://www.science-education.org/classroom_activities/chlorine_compound/epibatidine.html

3. Matthew J. Dowd, Department of Medicinal Chemistry of
Virginia Commonwealth University, http://www.phc.vcu.edu/Feature/oldfeature/epi/

4 Chris A Broka, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''20''', 3251-3254, {{DOI|10.1016/S0040-4039(00)73674-4}}

5. Dao Fei Huang, T. Y. Shen, ''Tetrahedron Lett.'', 1993, Volume '''34''', Issue '''28''', 4477-4480, {{DOI|10.1016/0040-4039(93)88063-O}}

File:Huang scheme.gif

2006-11-04T12:16:38Z

Ckp05: Huang and Shen Synthesis

Huang and Shen Synthesis

File:Corey steps 6 7 8 9.gif

2006-11-04T12:15:16Z

Ckp05: Corey Synthesis: Final Stages

Corey Synthesis: Final Stages

File:Corey steps 3 4 5.gif

2006-11-04T12:13:24Z

Ckp05: Corey Synthesis: Middle Stages

Corey Synthesis: Middle Stages

File:Corey steps 1 2.gif

2006-11-04T12:12:31Z

Ckp05:

Talk:It:Bufotoxin

2006-10-31T13:58:53Z

Ckp05: My thoughts

'''Ckp05''': Hi Yp305. I am just checking something. Have you checked that the information you have added (in the abstract) is about the same bufotoxin (vulgarobufotoxin) as that found in the toad Bufo Vulgaris? It may well be the same one because I found out that some toads have the same bufotoxins, its just that you mentioned a different species (Bufo Americus) and I thought it may be about a different bufotoxin. If you find that it is about a different bufotoxin, then you could create a new title under Bufotoxins in general, or add a link to a separate page (e.g. add a related compound column to the table and then put the different bufotoxin there).

It:Epibatidine

2006-10-30T14:19:59Z

Ckp05: Table text edit

It:Epibatidine

2006-10-30T14:18:12Z

Ckp05: Addition of Epibatidine Table

It:Amphidinolide T1

2006-10-30T14:11:07Z

Ckp05: Table Text Edit

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" |Beilstein Registry number
| colspan="2" |8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[nuclear magnetic resonance spectroscopy|NMR]], [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| colspan="2" |Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

===Ghosh’s Synthesis – Ring Formation via Macrolactonisation===

This synthesis strategy is based on producing two fragments of similar complexity and then combining them via Fragment coupling to provide the desired final product.

Scheme 1 involves the production of the target sulfone and Scheme 2 provides the sily enol ether product. These two compounds were subjected to a Lewis acid-mediated alkylation reaction. The TBS and benzyl groups were removed and macrolactonisation followed. Zinc was then used to perform a reductive cleavage of the product of the former process and the desired product was thus achieved.

[[Image:Scheme6.JPEG|thumb|left|200|Ghosh's Synthesis: Scheme 1]]

[[Image:Scheme7.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 2]]

[[Image:Scheme8.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 3]]

===Jamison’s Synthesis – Usage of Nickel-catalysed reductive coupling reactions of alkynes===

In this synthesis a carboxylic acid (36) and a homo allylic alcohol (37) were produced independently and then combined to follow a pathway to the final product. Compound 36 was synthesised from lactol. Compound 37 was produced by an alkyne-epoxide fragment coupling reaction of the alkyne (38) and the epoxide (39)

[[Image:Jamison_1.jpeg|thumb|left|200|Production of Fragments 36 and 37]]

Compounds 36 and 37 were coupled via a DCC-mediated esterification reaction, followed by removal of the TBS group and an oxidation reaction. A reductive macrocyclisation reaction yielded compound 34.

[[Image:Jamison_2.jpeg|thumb|left|200|Fragment Coupling of 36 and 37]]

In the penultimate step, TBS protection of the hydroxyl group followed by ozonolysis then produced the diketone (45). The final step involved selective methylenation followed by the removal of the TBS protective group, to produce Amphidinolide T1.

[[Image:Jamison_3.JPG|thumb|left|200|Final steps to produce Amphidinolide T1]]

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

File:Epibatidine.gif

2006-10-30T13:56:57Z

Ckp05: 2D Structure of epibatidine

2D Structure of epibatidine

It:projects

2006-10-30T12:03:45Z

Ckp05: Creating new Epibatidine page

__FORCETOC__

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! bgcolor="cyan" |Project<br /> Number
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|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
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|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
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|-
| bgcolor="#CCFF00" |06
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|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
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|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
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| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
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| bgcolor="#CCFF00" |20
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----
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----
[[Template:Chem-Data]]

It:name of project

2006-10-30T11:58:42Z

Ckp05: creating Epibatidine project

[[it:Epibatidine|Epibatidine]]

It:Bufotoxin

2006-10-28T15:23:37Z

Ckp05: Addition of Smile String to Table

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
! Smile String
| O=C1/C=C(\C=C/O1)C3C(OC(C)=O)CC4(O)C5CCC2CC(OC(=O)CCCCCCC(=O)NC(CC(O)=O)CCNC(N)=N)CCC2(C)C5CCC34C
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Amphidinolide T1

2006-10-28T10:49:35Z

Ckp05: layout edit

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

===Ghosh’s Synthesis – Ring Formation via Macrolactonisation===

This synthesis strategy is based on producing two fragments of similar complexity and then combining them via Fragment coupling to provide the desired final product.

Scheme 1 involves the production of the target sulfone and Scheme 2 provides the sily enol ether product. These two compounds were subjected to a Lewis acid-mediated alkylation reaction. The TBS and benzyl groups were removed and macrolactonisation followed. Zinc was then used to perform a reductive cleavage of the product of the former process and the desired product was thus achieved.

[[Image:Scheme6.JPEG|thumb|left|200|Ghosh's Synthesis: Scheme 1]]

[[Image:Scheme7.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 2]]

[[Image:Scheme8.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 3]]

===Jamison’s Synthesis – Usage of Nickel-catalysed reductive coupling reactions of alkynes===

In this synthesis a carboxylic acid (36) and a homo allylic alcohol (37) were produced independently and then combined to follow a pathway to the final product. Compound 36 was synthesised from lactol. Compound 37 was produced by an alkyne-epoxide fragment coupling reaction of the alkyne (38) and the epoxide (39)

[[Image:Jamison_1.jpeg|thumb|left|200|Production of Fragments 36 and 37]]

Compounds 36 and 37 were coupled via a DCC-mediated esterification reaction, followed by removal of the TBS group and an oxidation reaction. A reductive macrocyclisation reaction yielded compound 34.

[[Image:Jamison_2.jpeg|thumb|left|200|Fragment Coupling of 36 and 37]]

In the penultimate step, TBS protection of the hydroxyl group followed by ozonolysis then produced the diketone (45). The final step involved selective methylenation followed by the removal of the TBS protective group, to produce Amphidinolide T1.

[[Image:Jamison_3.JPG|thumb|left|200|Final steps to produce Amphidinolide T1]]

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

It:Amphidinolide T1

2006-10-28T10:36:51Z

Ckp05: layout edit

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

===Ghosh’s Synthesis – Ring Formation via Macrolactonisation===

This synthesis strategy is based on producing two fragments of similar complexity and then combining them via Fragment coupling to provide the desired final product.

Scheme 1 involves the production of the target sulfone and Scheme 2 provides the sily enol ether product. These two compounds were subjected to a Lewis acid-mediated alkylation reaction. The TBS and benzyl groups were removed and macrolactonisation followed. Zinc was then used to perform a reductive cleavage of the product of the former process and the desired product was thus achieved.

[[Image:Scheme6.JPEG|thumb|left|200|Ghosh's Synthesis: Scheme 1]]

[[Image:Scheme7.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 2]]

[[Image:Scheme8.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 3]]

===Jamison’s Synthesis – Usage of Nickel-catalysed reductive coupling reactions of alkynes===

In this synthesis a carboxylic acid (36) and a homo allylic alcohol (37) were produced independently and then combined to follow a pathway to the final product. Compound 36 was synthesised from lactol. Compound 37 was produced by an alkyne-epoxide fragment coupling reaction of the alkyne (38) and the epoxide (39)

[[Image:Jamison_1.jpeg|thumb|left|200|Production of Fragments 36 and 37]]

Compounds 36 and 37 were coupled via a DCC-mediated esterification reaction, followed by removal of the TBS group and an oxidation reaction. A reductive macrocyclisation reaction yielded compound 34.

[[Image:Jamison_2.jpeg|thumb|left|200|Fragment Coupling of 36 and 37]]

In the penultimate step, TBS protection of the hydroxyl group followed by ozonolysis then produced the diketone (45). The final step involved selective methylenation followed by the removal of the TBS protective group, to produce Amphidinolide T1.

[[Image:Jamison_3.JPG|thumb|left|200|Final steps to produce Amphidinolide T1]]

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

It:Amphidinolide T1

2006-10-28T10:34:29Z

Ckp05: Addition of Jamison Synthesis

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

===Ghosh’s Synthesis – Ring Formation via Macrolactonisation===

This synthesis strategy is based on producing two fragments of similar complexity and then combining them via Fragment coupling to provide the desired final product.

Scheme 1 involves the production of the target sulfone and Scheme 2 provides the sily enol ether product. These two compounds were subjected to a Lewis acid-mediated alkylation reaction. The TBS and benzyl groups were removed and macrolactonisation followed. Zinc was then used to perform a reductive cleavage of the product of the former process and the desired product was thus achieved.

[[Image:Scheme6.JPEG|thumb|left|200|Ghosh's Synthesis: Scheme 1]]

[[Image:Scheme7.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 2]]

[[Image:Scheme8.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 3]]

===Jamison’s Synthesis – Usage of Nickel-catalysed reductive coupling reactions of alkynes===

In this synthesis a carboxylic acid (36) and a homo allylic alcohol (37) were produced independently and then combined to follow a pathway to the final product. Compound 36 was synthesised from lactol. Compound 37 was produced by an alkyne-epoxide fragment coupling reaction of the alkyne (38) and the epoxide (39)

[[Image:Jamison_1.jpeg|thumb|left|200|Production of Fragments 36 and 37]]

Compounds 36 and 37 were coupled via a DCC-mediated esterification reaction, followed by removal of the TBS group and an oxidation reaction. A reductive macrocyclisation reaction yielded compound 34.

[[Image:Jamison_2.jpeg|thumb|left|200|Fragment Coupling of 36 and 37]]

In the penultimate step, TBS protection of the hydroxyl group followed by ozonolysis then produced the diketone (45). The final step involved selective methylenation followed by the removal of the TBS protective group, to produce Amphidinolide T1.

[[Image:Jamison_3.jpeg|thumb|left|200|Final steps to produce Amphidinolide T1]]

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

File:Jamison 3.JPG

2006-10-28T10:24:37Z

Ckp05: Jamison 3

Jamison 3

File:Jamison 2.jpeg

2006-10-28T10:24:16Z

Ckp05: Jamison_2

Jamison_2

File:Jamison 1.jpeg

2006-10-28T10:23:56Z

Ckp05: Jamison_1

Jamison_1

It:Amphidinolide T1

2006-10-28T10:10:22Z

Ckp05: Addition of Ghosh's Reaction Scheme

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

===Ghosh’s Synthesis – Ring Formation via Macrolactonisation===

This synthesis strategy is based on producing two fragments of similar complexity and then combining them via Fragment coupling to provide the desired final product.

Scheme 1 involves the production of the target sulfone and Scheme 2 provides the sily enol ether product. These two compounds were subjected to a Lewis acid-mediated alkylation reaction. The TBS and benzyl groups were removed and macrolactonisation followed. Zinc was then used to perform a reductive cleavage of the product of the former process and the desired product was thus achieved.

[[Image:Scheme6.JPEG|thumb|left|200|Ghosh's Synthesis: Scheme 1]]

[[Image:Scheme7.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 2]]

[[Image:Scheme8.JPG|thumb|left|200|Ghosh's Synthesis: Scheme 3]]

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

File:Scheme8.JPG

2006-10-28T09:54:57Z

Ckp05: Ghosh's Synthesis: Scheme 3

Ghosh's Synthesis: Scheme 3

File:Scheme7.JPG

2006-10-28T09:54:25Z

Ckp05: Ghosh's Synthesis: Scheme 2

Ghosh's Synthesis: Scheme 2

File:Scheme6.JPEG

2006-10-28T09:53:17Z

Ckp05: Ghosh's Synthesis: Scheme 1

Ghosh's Synthesis: Scheme 1

It:Amphidinolide T1

2006-10-28T09:36:49Z

Ckp05: Addition of Fürster’s Synthesis

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==Synthesis==

===Fürster’s Synthesis – Utilising a late stage intermediate to produce the product===

A key intermediate was produced from three separate compounds that was fundamental to the overall synthesis strategy. This intermediate was then used to produce Amphidinolide T1 and could also be used the T3, T4 and T5 compounds of the amphidinolide family.

[[Image:Scheme1.JPEG|thumb|left|200|Fürster’s Strategy]]

Once the intermediate had been produced then a sequence of three steps was required to produce the desired product. This involved the removal of the silyl protective group, achieved via the aid of a flurosilicate reagent, the oxidation of the alcohol to the ketone on C-12 and the deprotection of the MOM ether by exposure to acidic Dowex resin.

[[Image:Furster_rxn_product.JPG|thumb|left|200|Reaction Scheme]]

<div align="left"><br>

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

File:Furster rxn product.JPG

2006-10-27T17:51:35Z

Ckp05: Amphidinolide T1 produced via an intermediate

Amphidinolide T1 produced via an intermediate

It:projects

2006-10-27T17:42:35Z

Ckp05: removing unwanted pic

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

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|-
| bgcolor="#CCFF00" |02
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|-
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|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
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*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
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*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
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== Overlaps ==

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make the changes there, and then copy the entire lot to the Wiki page to preview and then save. Tht way, if your contribution
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----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

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[[Template:Chem-Data]]

It:projects

2006-10-27T17:41:51Z

Ckp05: /* Sandbox (Play-Pen) */

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: Α, α, β Δ, δ
Try copying/pasting some of the [http://www.ch.ic.ac.uk/local/it/lab1.html examples in the course work] into this page. See the effect by selecting '''Show Preview'''. No not use '''Save Page''' so as to leave this area uncluttered for others.
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[[Image:scheme1.JPEG|thumb|right|200|Scheme 1]]

== Main Project Page ==
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{| summary="CIT Project Titles" border="1"
! bgcolor="cyan" |Project<br /> Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]
|-
| bgcolor="#CCFF00" |06
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]
|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]
|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H<sub>3</sub>N-BH<sub>3</sub> (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
*[[it:Serotonin|Serotonin, The 'HAPPY' Drug]]
*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
*[[it:Furosemide|Furosemide]]
*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
*[[it:Ferrocene|Ferrocene]]
*[[it:Scopolamine|Scopolamine, the (Former) Truth Drug]]
*[[it:Camptothecin|Camptothecin,Anti-cancer agent ]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own
''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If two people start editing a page at the same time, and '''save''' the change simultaneously, its possible only one of the changes
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One precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. Tht way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

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----
[[Template:Chem-Data]]

File:Scheme1.JPEG

2006-10-27T17:40:13Z

Ckp05: Scheme 1

Scheme 1

Nuclear magnetic resonance spectroscopy

2006-10-27T13:28:18Z

Ckp05: addition of C nmr spectrum

It:Amphidinolide T1

2006-10-27T13:26:02Z

Ckp05: changing back to one link for NMR spectra

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

Nuclear magnetic resonance spectroscopy

2006-10-27T13:23:16Z

Ckp05: addition of H nmr spectrum

[[Image:H_nmr_amphidinolideT1.gif|thumb|left|400|H NMR Spectrum of Amphidinolide T1]]

File:C nmr amphidinolideT1.gif

2006-10-27T13:19:45Z

Ckp05: 13C NMR Spectrum of Amphidinolide T1

13C NMR Spectrum of Amphidinolide T1

File:H nmr amphidinolideT1.gif

2006-10-27T13:18:35Z

Ckp05: H NMR Spectrum of Amphidinolide T1

H NMR Spectrum of Amphidinolide T1

Mass spectrometry

2006-10-27T13:17:15Z

Ckp05: removal of unwanted item

Infrared spectroscopy

2006-10-27T13:16:17Z

Ckp05: removal of unwanted item

It:Amphidinolide T1

2006-10-27T13:15:48Z

Ckp05: changing of nmr link to 1H and 13C nmr links in table

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|<sup>1</sup>H NMR]], [[nuclear magnetic resonance spectroscopy|<sup>13</sup>C NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

It:Bufotoxin

2006-10-27T10:01:39Z

Ckp05: text edit

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|Proposed vulgaro butotoxin structure by Wieland]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-26T16:14:19Z

Ckp05: change of layout+2nd pic of sketch of bufo vulgaris

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="left"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
[[Image:Bufo@vulgaris.jpeg|thumb|left|250|Sketch of Bufo vulgaris (top left), by George Albert Boulenger, 1897-98]]
<div align="left"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}
<div align="left"><br>
The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|vulgaro butotoxin]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

File:Bufo@vulgaris.jpeg

2006-10-26T16:00:40Z

Ckp05: Sketch of Bufo Vulgaris by George Albert Boulenger, (1897-1898)

Sketch of Bufo Vulgaris by George Albert Boulenger, (1897-1898)

It:Bufotoxin

2006-10-26T15:52:23Z

Ckp05: text edit

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="right"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|Picture of Bufo vulgaris mating]]
<div align="right"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}

The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|vulgaro butotoxin]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Bufotoxin

2006-10-26T15:45:53Z

Ckp05: added real life pic of bufo vulgaris

==Bufotoxin and the toad, ''Bufo vulgaris''==
<div align="right"><br>
[[Image:bufovulgaris.jpg|thumb|left|250|real life pic of bufo vulgaris mating]]
<div align="right"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}

The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|vulgaro butotoxin]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

File:Bufovulgaris.jpg

2006-10-26T15:40:41Z

Ckp05: real life pic of bufo vulgaris mating

real life pic of bufo vulgaris mating

It:Bufotoxin

2006-10-26T14:10:44Z

Ckp05: removal of unwanted text

==Bufotoxin and the toad, ''Bufo vulgaris''==

<div align="right"><br>
{| border="1"
|+ Classification:
|-
! Kingdom
| Animalia
|-
! Phylum
| Chordata
|-
! Class
| Amphibia
|-
! Order
| Anura
|-
! Family
| Bufonidae
|-
! Genus
| ''Bufo''
|-
! Species
| '''''B. vulgaris'''''
|}

The toad ''Bufo vulgaris'', as scientifically classified to the upper right, (also known as ''Bufo bufo bufo'' or ''Bufo bufo bufo linné'' or simply the “Common European Toad”) contains a particular type of bufotoxin. Bufotoxins are a group of toxic substances that are found in many toads that belong to the ''Bufo'' genus. These milky fluids are secreted via the parotoid glands and are also found in the skin and venom of many toads that belong to the ''Bufo'' genus. Bufotoxins can consist of various molecules that include: 5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin. They also vary in the relative proportions of these molecules that make up the unique composition of a bufotoxin found in each species. The three major components of most bufotoxins are bufagin, (which can cause deadly disturbances of the heart and acts in an analogous fashion to digitalis), bufotenine (a hallucinogen) and serotonin (a vasoconstrictor). Adding to the ambiguity of the term, bufotoxin can also be used to describe the conjugate of a bufagin with suberylarginine (Chen & Kovarikova, 1967).<sup>1+2</sup>

The particular bufotoxin found in the toad, ''Bufo vulgaris'', also known as vulgaro-bufotoxin, was isolated by Wieland and his colleagues in 1922 and a tentative structure was proposed. He concluded that a molecule of vulgaro bufotoxin consisted of bufotalin and suberyl-arginine.<sup>3+4</sup> The Reichstein group later re-confirmed the isolation of vulgaro-bufotoxin in 1955, the correct structure was then proposed by Yoshiaki Kamano, some 30 years later.<sup>6</sup>

<div align="left"><br>
==2D & 3D Structures of Vulgarobufotoxin==

Below are the original 2D and 3D proposed structures of vulgarobufotoxin by Wieland in 1922. The correct molecular formula was obtained, C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>

[[Image:2D_vulbuf.gif|thumb|right|150|vulgaro butotoxin]]

<div align="left"><br>
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000

HEADER 3D vulgaro bufotoxin 23-Oct-06 NONE 1
TITLE vulgaro bufotoxin NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 O 0 1.762 -1.981 3.563 0.00 0.00 O+0
ATOM 2 C 0 2.399 -2.796 2.919 0.00 0.00 C+0
ATOM 3 C 0 3.317 -2.361 1.946 0.00 0.00 C+0
ATOM 4 C 0 4.020 -3.290 1.236 0.00 0.00 C+0
ATOM 5 C 0 3.807 -4.653 1.500 0.00 0.00 C+0
ATOM 6 C 0 2.916 -5.025 2.443 0.00 0.00 C+0
ATOM 7 O 0 2.230 -4.110 3.143 0.00 0.00 O+0
ATOM 8 C 0 5.005 -2.863 0.193 0.00 0.00 C+0
ATOM 9 C 0 4.405 -3.020 -1.229 0.00 0.00 C+0
ATOM 10 O 0 3.115 -3.680 -1.154 0.00 0.00 O+0
ATOM 11 C 0 2.691 -4.443 -2.173 0.00 0.00 C+0
ATOM 12 C 0 1.351 -5.129 -2.096 0.00 0.00 C+0
ATOM 13 O 0 3.384 -4.581 -3.154 0.00 0.00 O+0
ATOM 14 C 0 4.240 -1.587 -1.804 0.00 0.00 C+0
ATOM 15 C 0 4.275 -0.703 -0.546 0.00 0.00 C+0
ATOM 16 O 0 2.986 -0.841 0.141 0.00 0.00 O+0
ATOM 17 C 0 1.859 -0.425 -0.458 0.00 0.00 C+0
ATOM 18 O 0 1.903 0.041 -1.572 0.00 0.00 O+0
ATOM 19 C 0 0.538 -0.538 0.259 0.00 0.00 C+0
ATOM 20 C 0 -0.557 0.120 -0.582 0.00 0.00 C+0
ATOM 21 C 0 -1.873 0.113 0.198 0.00 0.00 C+0
ATOM 22 C 0 -2.995 0.659 -0.688 0.00 0.00 C+0
ATOM 23 C 0 -4.311 0.652 0.092 0.00 0.00 C+0
ATOM 24 C 0 -5.432 1.198 -0.794 0.00 0.00 C+0
ATOM 25 C 0 -6.728 1.191 -0.025 0.00 0.00 C+0
ATOM 26 O 0 -6.753 0.788 1.119 0.00 0.00 O+0
ATOM 27 N 0 -7.860 1.632 -0.609 0.00 0.00 N+0
ATOM 28 C 0 -9.097 1.728 0.171 0.00 0.00 C+0
ATOM 29 C 0 -9.671 3.141 0.044 0.00 0.00 C+0
ATOM 30 C 0 -8.736 4.124 0.701 0.00 0.00 C+0
ATOM 31 O 0 -9.077 5.419 0.786 0.00 0.00 O+0
ATOM 32 O 0 -7.681 3.746 1.151 0.00 0.00 O+0
ATOM 33 C 0 -10.114 0.715 -0.358 0.00 0.00 C+0
ATOM 34 C 0 -9.593 -0.704 -0.117 0.00 0.00 C+0
ATOM 35 N 0 -10.567 -1.674 -0.623 0.00 0.00 N+0
ATOM 36 C 0 -10.314 -3.021 -0.517 0.00 0.00 C+0
ATOM 37 N 0 -11.228 -3.932 -0.992 0.00 0.00 N+0
ATOM 38 N 0 -9.208 -3.435 0.035 0.00 0.00 N+0
ATOM 39 C 0 4.518 0.761 -0.767 0.00 0.00 C+0
ATOM 40 C 0 4.991 1.146 -2.164 0.00 0.00 C+0
ATOM 41 C 0 4.965 2.681 -2.253 0.00 0.00 C+0
ATOM 42 C 0 5.868 3.285 -1.184 0.00 0.00 C+0
ATOM 43 C 0 5.894 4.807 -1.290 0.00 0.00 C+0
ATOM 44 C 0 6.904 5.367 -0.286 0.00 0.00 C+0
ATOM 45 O 0 6.905 6.795 -0.362 0.00 0.00 O+0
ATOM 46 C 0 6.539 4.932 1.131 0.00 0.00 C+0
ATOM 47 C 0 6.471 3.410 1.226 0.00 0.00 C+0
ATOM 48 C 0 5.451 2.855 0.226 0.00 0.00 C+0
ATOM 49 C 0 4.061 3.368 0.579 0.00 0.00 C+0
ATOM 50 C 0 5.494 1.324 0.265 0.00 0.00 C+0
ATOM 51 C 0 5.219 0.738 1.636 0.00 0.00 C+0
ATOM 52 C 0 5.501 -0.777 1.656 0.00 0.00 C+0
ATOM 53 C 0 5.387 -1.376 0.282 0.00 0.00 C+0
ATOM 54 C 0 6.750 -1.285 -0.434 0.00 0.00 C+0
ATOM 55 H 0 3.462 -1.307 1.762 0.00 0.00 H+0
ATOM 56 H 0 4.354 -5.403 0.948 0.00 0.00 H+0
ATOM 57 H 0 2.757 -6.075 2.641 0.00 0.00 H+0
ATOM 58 H 0 5.918 -3.464 0.269 0.00 0.00 H+0
ATOM 59 H 0 5.084 -3.598 -1.856 0.00 0.00 H+0
ATOM 60 H 0 0.875 -4.889 -1.145 0.00 0.00 H+0
ATOM 61 H 0 0.720 -4.786 -2.915 0.00 0.00 H+0
ATOM 62 H 0 1.490 -6.208 -2.171 0.00 0.00 H+0
ATOM 63 H 0 5.044 -1.341 -2.489 0.00 0.00 H+0
ATOM 64 H 0 3.274 -1.489 -2.305 0.00 0.00 H+0
ATOM 65 H 0 0.296 -1.590 0.411 0.00 0.00 H+0
ATOM 66 H 0 0.605 -0.038 1.225 0.00 0.00 H+0
ATOM 67 H 0 -0.274 1.149 -0.807 0.00 0.00 H+0
ATOM 68 H 0 -0.683 -0.433 -1.513 0.00 0.00 H+0
ATOM 69 H 0 -2.112 -0.908 0.498 0.00 0.00 H+0
ATOM 70 H 0 -1.774 0.738 1.085 0.00 0.00 H+0
ATOM 71 H 0 -2.756 1.680 -0.988 0.00 0.00 H+0
ATOM 72 H 0 -3.095 0.034 -1.575 0.00 0.00 H+0
ATOM 73 H 0 -4.549 -0.369 0.392 0.00 0.00 H+0
ATOM 74 H 0 -4.211 1.277 0.979 0.00 0.00 H+0
ATOM 75 H 0 -5.193 2.219 -1.094 0.00 0.00 H+0
ATOM 76 H 0 -5.532 0.573 -1.681 0.00 0.00 H+0
ATOM 77 H 0 -7.856 1.885 -1.545 0.00 0.00 H+0
ATOM 78 H 0 -8.883 1.516 1.219 0.00 0.00 H+0
ATOM 79 H 0 -9.782 3.394 -1.010 0.00 0.00 H+0
ATOM 80 H 0 -10.644 3.183 0.532 0.00 0.00 H+0
ATOM 81 H 0 -8.477 6.050 1.207 0.00 0.00 H+0
ATOM 82 H 0 -11.063 0.847 0.162 0.00 0.00 H+0
ATOM 83 H 0 -10.261 0.871 -1.427 0.00 0.00 H+0
ATOM 84 H 0 -8.644 -0.836 -0.637 0.00 0.00 H+0
ATOM 85 H 0 -9.446 -0.860 0.952 0.00 0.00 H+0
ATOM 86 H 0 -11.390 -1.366 -1.034 0.00 0.00 H+0
ATOM 87 H 0 -12.051 -3.624 -1.403 0.00 0.00 H+0
ATOM 88 H 0 -11.050 -4.882 -0.917 0.00 0.00 H+0
ATOM 89 H 0 -9.030 -4.386 0.111 0.00 0.00 H+0
ATOM 90 H 0 3.533 1.252 -0.626 0.00 0.00 H+0
ATOM 91 H 0 6.006 0.794 -2.330 0.00 0.00 H+0
ATOM 92 H 0 4.320 0.731 -2.913 0.00 0.00 H+0
ATOM 93 H 0 5.328 2.977 -3.241 0.00 0.00 H+0
ATOM 94 H 0 3.943 3.032 -2.135 0.00 0.00 H+0
ATOM 95 H 0 6.892 2.916 -1.357 0.00 0.00 H+0
ATOM 96 H 0 6.210 5.089 -2.301 0.00 0.00 H+0
ATOM 97 H 0 4.911 5.229 -1.106 0.00 0.00 H+0
ATOM 98 H 0 7.900 4.995 -0.534 0.00 0.00 H+0
ATOM 99 H 0 7.552 7.109 0.284 0.00 0.00 H+0
ATOM 100 H 0 7.313 5.293 1.820 0.00 0.00 H+0
ATOM 101 H 0 5.591 5.378 1.425 0.00 0.00 H+0
ATOM 102 H 0 7.453 2.988 1.004 0.00 0.00 H+0
ATOM 103 H 0 6.178 3.122 2.236 0.00 0.00 H+0
ATOM 104 H 0 4.054 4.457 0.537 0.00 0.00 H+0
ATOM 105 H 0 3.336 2.972 -0.132 0.00 0.00 H+0
ATOM 106 H 0 3.798 3.041 1.585 0.00 0.00 H+0
ATOM 107 H 0 6.522 1.076 -0.030 0.00 0.00 H+0
ATOM 108 H 0 5.858 1.224 2.381 0.00 0.00 H+0
ATOM 109 H 0 4.176 0.908 1.918 0.00 0.00 H+0
ATOM 110 H 0 6.522 -0.938 2.040 0.00 0.00 H+0
ATOM 111 H 0 4.814 -1.240 2.369 0.00 0.00 H+0
ATOM 112 H 0 7.473 -1.921 0.077 0.00 0.00 H+0
ATOM 113 H 0 6.641 -1.617 -1.467 0.00 0.00 H+0
ATOM 114 H 0 7.101 -0.253 -0.419 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 119
CONECT 2 1 7 3 0 NONE 120
CONECT 3 2 4 55 0 NONE 121
CONECT 4 3 5 8 0 NONE 122
CONECT 5 4 6 56 0 NONE 123
CONECT 6 5 7 57 0 NONE 124
CONECT 7 6 2 0 0 NONE 125
CONECT 8 4 53 9 58 NONE 126
CONECT 9 8 10 14 59 NONE 127
CONECT 10 9 11 0 0 NONE 128
CONECT 11 10 12 13 0 NONE 129
CONECT 12 11 60 61 62 NONE 130
CONECT 13 11 0 0 0 NONE 131
CONECT 14 9 15 63 64 NONE 132
CONECT 15 14 53 16 39 NONE 133
CONECT 16 15 17 0 0 NONE 134
CONECT 17 16 18 19 0 NONE 135
CONECT 18 17 0 0 0 NONE 136
CONECT 19 17 20 65 66 NONE 137
CONECT 20 19 21 67 68 NONE 138
CONECT 21 20 22 69 70 NONE 139
CONECT 22 21 23 71 72 NONE 140
CONECT 23 22 24 73 74 NONE 141
CONECT 24 23 25 75 76 NONE 142
CONECT 25 24 26 27 0 NONE 143
CONECT 26 25 0 0 0 NONE 144
CONECT 27 25 28 77 0 NONE 145
CONECT 28 27 29 33 78 NONE 146
CONECT 29 28 30 79 80 NONE 147
CONECT 30 29 31 32 0 NONE 148
CONECT 31 30 81 0 0 NONE 149
CONECT 32 30 0 0 0 NONE 150
CONECT 33 28 34 82 83 NONE 151
CONECT 34 33 35 84 85 NONE 152
CONECT 35 34 36 86 0 NONE 153
CONECT 36 35 37 38 0 NONE 154
CONECT 37 36 87 88 0 NONE 155
CONECT 38 36 89 0 0 NONE 156
CONECT 39 15 50 40 90 NONE 157
CONECT 40 39 41 91 92 NONE 158
CONECT 41 40 42 93 94 NONE 159
CONECT 42 41 48 43 95 NONE 160
CONECT 43 42 44 96 97 NONE 161
CONECT 44 43 45 46 98 NONE 162
CONECT 45 44 99 0 0 NONE 163
CONECT 46 44 47 100 101 NONE 164
CONECT 47 46 48 102 103 NONE 165
CONECT 48 47 42 49 50 NONE 166
CONECT 49 48 104 105 106 NONE 167
CONECT 50 48 39 51 107 NONE 168
CONECT 51 50 52 108 109 NONE 169
CONECT 52 51 53 110 111 NONE 170
CONECT 53 52 8 15 54 NONE 171
CONECT 54 53 112 113 114 NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

It was later discovered that the correct structure of bufotoxin involved the swapping of the -OH group and the long chain in relation to Wielands original devised structure.<sup>5+6</sup> This can be seen in the 3D structure below and the 2D structure below.

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 23-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 23-Oct-06 0 NONE 4
ATOM 1 C 0 4.020 3.244 -2.877 0.00 0.00 C+0
ATOM 2 C 0 4.138 2.111 -1.855 0.00 0.00 C+0
ATOM 3 C 0 3.846 2.654 -0.455 0.00 0.00 C+0
ATOM 4 C 0 4.854 3.754 -0.114 0.00 0.00 C+0
ATOM 5 C 0 6.270 3.171 -0.144 0.00 0.00 C+0
ATOM 6 C 0 6.199 1.687 -0.507 0.00 0.00 C+0
ATOM 7 C 0 5.555 1.536 -1.894 0.00 0.00 C+0
ATOM 8 C 0 5.513 0.077 -2.336 0.00 0.00 C+0
ATOM 9 C 0 6.911 -0.564 -2.291 0.00 0.00 C+0
ATOM 10 C 0 7.427 -0.421 -0.872 0.00 0.00 C+0
ATOM 11 C 0 6.419 -1.022 0.108 0.00 0.00 C+0
ATOM 12 C 0 7.594 1.096 -0.590 0.00 0.00 C+0
ATOM 13 O 0 8.351 1.719 -1.630 0.00 0.00 O+0
ATOM 14 C 0 8.393 1.082 0.718 0.00 0.00 C+0
ATOM 15 C 0 9.429 -0.050 0.479 0.00 0.00 C+0
ATOM 16 O 0 9.656 -0.785 1.711 0.00 0.00 O+0
ATOM 17 C 0 10.641 -0.412 2.543 0.00 0.00 C+0
ATOM 18 C 0 10.877 -1.175 3.821 0.00 0.00 C+0
ATOM 19 O 0 11.339 0.535 2.268 0.00 0.00 O+0
ATOM 20 C 0 8.817 -0.984 -0.593 0.00 0.00 C+0
ATOM 21 C 0 8.713 -2.390 -0.062 0.00 0.00 C+0
ATOM 22 C 0 8.137 -2.626 1.199 0.00 0.00 C+0
ATOM 23 C 0 8.053 -3.907 1.658 0.00 0.00 C+0
ATOM 24 C 0 9.167 -3.426 -0.798 0.00 0.00 C+0
ATOM 25 O 0 9.083 -4.685 -0.344 0.00 0.00 O+0
ATOM 26 C 0 8.545 -4.954 0.857 0.00 0.00 C+0
ATOM 27 O 0 8.479 -6.106 1.251 0.00 0.00 O+0
ATOM 28 C 0 2.429 3.230 -0.417 0.00 0.00 C+0
ATOM 29 C 0 1.422 2.130 -0.758 0.00 0.00 C+0
ATOM 30 O 0 0.078 2.676 -0.722 0.00 0.00 O+0
ATOM 31 C 0 -0.958 1.890 -0.388 0.00 0.00 C+0
ATOM 32 C 0 -2.353 2.457 -0.351 0.00 0.00 C+0
ATOM 33 C 0 -3.339 1.360 0.055 0.00 0.00 C+0
ATOM 34 C 0 -4.756 1.935 0.093 0.00 0.00 C+0
ATOM 35 C 0 -5.742 0.838 0.499 0.00 0.00 C+0
ATOM 36 C 0 -7.159 1.414 0.537 0.00 0.00 C+0
ATOM 37 C 0 -8.145 0.316 0.943 0.00 0.00 C+0
ATOM 38 C 0 -9.540 0.884 0.981 0.00 0.00 C+0
ATOM 39 N 0 -10.580 0.094 1.316 0.00 0.00 N+0
ATOM 40 C 0 -11.937 0.645 1.352 0.00 0.00 C+0
ATOM 41 C 0 -12.950 -0.480 1.135 0.00 0.00 C+0
ATOM 42 C 0 -12.784 -1.052 -0.274 0.00 0.00 C+0
ATOM 43 C 0 -13.797 -2.177 -0.491 0.00 0.00 C+0
ATOM 44 N 0 -13.637 -2.724 -1.841 0.00 0.00 N+0
ATOM 45 C 0 -14.445 -3.753 -2.265 0.00 0.00 C+0
ATOM 46 N 0 -15.403 -4.267 -1.424 0.00 0.00 N+0
ATOM 47 H 0 -15.973 -4.993 -1.723 0.00 0.00 H+0
ATOM 48 N 0 -14.303 -4.240 -3.466 0.00 0.00 N+0
ATOM 49 H 0 -14.873 -4.965 -3.766 0.00 0.00 H+0
ATOM 50 C 0 -12.181 1.290 2.692 0.00 0.00 C+0
ATOM 51 O 0 -13.306 1.836 2.941 0.00 0.00 O+0
ATOM 52 O 0 -11.263 1.289 3.577 0.00 0.00 O+0
ATOM 53 O 0 -9.728 2.051 0.710 0.00 0.00 O+0
ATOM 54 O 0 -0.771 0.727 -0.118 0.00 0.00 O+0
ATOM 55 C 0 1.715 1.586 -2.158 0.00 0.00 C+0
ATOM 56 C 0 3.132 1.010 -2.196 0.00 0.00 C+0
ATOM 57 H 0 4.738 4.028 -2.634 0.00 0.00 H+0
ATOM 58 H 0 4.229 2.856 -3.874 0.00 0.00 H+0
ATOM 59 H 0 3.011 3.654 -2.850 0.00 0.00 H+0
ATOM 60 H 0 3.929 1.847 0.272 0.00 0.00 H+0
ATOM 61 H 0 4.776 4.558 -0.846 0.00 0.00 H+0
ATOM 62 H 0 4.643 4.145 0.881 0.00 0.00 H+0
ATOM 63 H 0 6.865 3.700 -0.889 0.00 0.00 H+0
ATOM 64 H 0 6.730 3.285 0.837 0.00 0.00 H+0
ATOM 65 H 0 5.603 1.156 0.235 0.00 0.00 H+0
ATOM 66 H 0 6.143 2.097 -2.620 0.00 0.00 H+0
ATOM 67 H 0 4.846 -0.477 -1.675 0.00 0.00 H+0
ATOM 68 H 0 5.129 0.023 -3.354 0.00 0.00 H+0
ATOM 69 H 0 6.844 -1.619 -2.556 0.00 0.00 H+0
ATOM 70 H 0 7.578 -0.048 -2.982 0.00 0.00 H+0
ATOM 71 H 0 6.378 -2.103 -0.029 0.00 0.00 H+0
ATOM 72 H 0 6.726 -0.796 1.129 0.00 0.00 H+0
ATOM 73 H 0 5.433 -0.595 -0.077 0.00 0.00 H+0
ATOM 74 H 0 8.422 2.656 -1.401 0.00 0.00 H+0
ATOM 75 H 0 8.894 2.037 0.874 0.00 0.00 H+0
ATOM 76 H 0 7.747 0.842 1.562 0.00 0.00 H+0
ATOM 77 H 0 10.367 0.372 0.118 0.00 0.00 H+0
ATOM 78 H 0 10.156 -1.989 3.897 0.00 0.00 H+0
ATOM 79 H 0 11.887 -1.584 3.819 0.00 0.00 H+0
ATOM 80 H 0 10.758 -0.505 4.672 0.00 0.00 H+0
ATOM 81 H 0 9.421 -0.966 -1.500 0.00 0.00 H+0
ATOM 82 H 0 7.767 -1.805 1.795 0.00 0.00 H+0
ATOM 83 H 0 7.616 -4.116 2.624 0.00 0.00 H+0
ATOM 84 H 0 9.604 -3.238 -1.768 0.00 0.00 H+0
ATOM 85 H 0 2.221 3.618 0.580 0.00 0.00 H+0
ATOM 86 H 0 2.346 4.037 -1.145 0.00 0.00 H+0
ATOM 87 H 0 1.506 1.323 -0.030 0.00 0.00 H+0
ATOM 88 H 0 -2.396 3.270 0.374 0.00 0.00 H+0
ATOM 89 H 0 -2.618 2.836 -1.338 0.00 0.00 H+0
ATOM 90 H 0 -3.297 0.547 -0.670 0.00 0.00 H+0
ATOM 91 H 0 -3.074 0.980 1.042 0.00 0.00 H+0
ATOM 92 H 0 -4.799 2.748 0.818 0.00 0.00 H+0
ATOM 93 H 0 -5.021 2.315 -0.894 0.00 0.00 H+0
ATOM 94 H 0 -5.699 0.025 -0.226 0.00 0.00 H+0
ATOM 95 H 0 -5.477 0.459 1.486 0.00 0.00 H+0
ATOM 96 H 0 -7.201 2.227 1.262 0.00 0.00 H+0
ATOM 97 H 0 -7.424 1.793 -0.450 0.00 0.00 H+0
ATOM 98 H 0 -8.102 -0.497 0.219 0.00 0.00 H+0
ATOM 99 H 0 -7.880 -0.063 1.930 0.00 0.00 H+0
ATOM 100 H 0 -10.430 -0.840 1.533 0.00 0.00 H+0
ATOM 101 H 0 -12.047 1.391 0.565 0.00 0.00 H+0
ATOM 102 H 0 -12.782 -1.268 1.869 0.00 0.00 H+0
ATOM 103 H 0 -13.960 -0.086 1.250 0.00 0.00 H+0
ATOM 104 H 0 -12.952 -0.264 -1.008 0.00 0.00 H+0
ATOM 105 H 0 -11.774 -1.445 -0.389 0.00 0.00 H+0
ATOM 106 H 0 -13.628 -2.965 0.243 0.00 0.00 H+0
ATOM 107 H 0 -14.807 -1.783 -0.376 0.00 0.00 H+0
ATOM 108 H 0 -12.962 -2.361 -2.435 0.00 0.00 H+0
ATOM 109 H 0 -15.509 -3.905 -0.530 0.00 0.00 H+0
ATOM 110 H 0 0.997 0.803 -2.400 0.00 0.00 H+0
ATOM 111 H 0 1.631 2.393 -2.886 0.00 0.00 H+0
ATOM 112 H 0 3.340 0.623 -3.194 0.00 0.00 H+0
ATOM 113 H 0 3.215 0.203 -1.468 0.00 0.00 H+0
CONECT 1 2 57 58 59 NONE 118
CONECT 2 1 56 7 3 NONE 119
CONECT 3 2 4 28 60 NONE 120
CONECT 4 3 5 61 62 NONE 121
CONECT 5 4 6 63 64 NONE 122
CONECT 6 5 12 7 65 NONE 123
CONECT 7 6 2 8 66 NONE 124
CONECT 8 7 9 67 68 NONE 125
CONECT 9 8 10 69 70 NONE 126
CONECT 10 9 20 11 12 NONE 127
CONECT 11 10 71 72 73 NONE 128
CONECT 12 10 13 6 14 NONE 129
CONECT 13 12 74 0 0 NONE 130
CONECT 14 12 15 75 76 NONE 131
CONECT 15 14 16 20 77 NONE 132
CONECT 16 15 17 0 0 NONE 133
CONECT 17 16 18 19 0 NONE 134
CONECT 18 17 78 79 80 NONE 135
CONECT 19 17 0 0 0 NONE 136
CONECT 20 15 10 21 81 NONE 137
CONECT 21 20 22 24 0 NONE 138
CONECT 22 21 23 82 0 NONE 139
CONECT 23 22 26 83 0 NONE 140
CONECT 24 21 25 84 0 NONE 141
CONECT 25 24 26 0 0 NONE 142
CONECT 26 25 23 27 0 NONE 143
CONECT 27 26 0 0 0 NONE 144
CONECT 28 3 29 85 86 NONE 145
CONECT 29 28 30 55 87 NONE 146
CONECT 30 29 31 0 0 NONE 147
CONECT 31 30 32 54 0 NONE 148
CONECT 32 31 33 88 89 NONE 149
CONECT 33 32 34 90 91 NONE 150
CONECT 34 33 35 92 93 NONE 151
CONECT 35 34 36 94 95 NONE 152
CONECT 36 35 37 96 97 NONE 153
CONECT 37 36 38 98 99 NONE 154
CONECT 38 37 39 53 0 NONE 155
CONECT 39 38 40 100 0 NONE 156
CONECT 40 39 41 50 101 NONE 157
CONECT 41 40 42 102 103 NONE 158
CONECT 42 41 43 104 105 NONE 159
CONECT 43 42 44 106 107 NONE 160
CONECT 44 43 45 108 0 NONE 161
CONECT 45 44 46 48 0 NONE 162
CONECT 46 45 47 109 0 NONE 163
CONECT 48 45 49 0 0 NONE 164
CONECT 50 40 51 52 0 NONE 165
CONECT 51 50 0 0 0 NONE 166
CONECT 52 50 0 0 0 NONE 167
CONECT 53 38 0 0 0 NONE 168
CONECT 54 31 0 0 0 NONE 169
CONECT 55 29 56 110 111 NONE 170
CONECT 56 55 2 112 113 NONE 171
NONE 172
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
<div align="left"><br>
[[Image:new_vulgaro_bufotoxin.jpg|thumb|right|150|vulgaro butotoxin]]

=='''Properties of Vulgarobutotoxin'''==

<div align="left"><br>
{| border="1"
|-
! Chemical name
| Bufotalin-3-suberoylargininester
|-
! Autoname/Iupac name
| 7-(1-carboxy-4-guanidino-butylcarbamoyl)-heptanoic acid 16-acetoxy-14-hydroxy-10,13-dimethyl-17-(6-oxo-6H-pyran-3-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
|-
! Molecular Formula
| C<sub>40</sub>H<sub>60</sub>N<sub>4</sub>O<sub>10</sub>
|-
! Molecular Weight
| 756.93
|-
! Stereo or non-stereo
| Stereo compound
|-
! Class of substance
| Heterocyclic
|-
|}

<div align="left"><br>
==Citations==

<div align="left"><br>
1. ''Wikipedia'', http://en.wikipedia.org/wiki/Bufotoxin.
<div align="left"><br>
2. ''Encyclopædia Britannica Online'',2006, http://www.britannica.com/eb/article-9017947.
<div align="left"><br>
3. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1929, '''1''', 397-401.
<div align="left"><br>
4. H. Jensen, K. K. Chen, ''Chemical Studies on Toad Poisons'', 1930, '''2''', 741-753.
<div align="left"><br>
5. Yoshiaki Kamano, Hiroshi Yamamoto, Yoshihiro Tanaka, Manki Komatsu, ''Tetrahedron Letters'', 1968, '''54''', 5673-5676.
<div align="left"><br>
6. Yoshiaki Kamano, George R. Pettit, Pavel Drasar, Masuo Inoue, John C. Knight, ''J. Org. Chem'', 1987, '''52''', 3573-3578.

It:Amphidinolide T1

2006-10-26T14:08:43Z

Ckp05: Adding DOI links to references

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, {{DOI|10.1021/ja042733f}}

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, {{DOI|10.1021/jo991393r}}

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, {{DOI|10.1016/S0040-4020(01)00591-9}}

It:Amphidinolide T1

2006-10-26T13:57:26Z

Ckp05: Addition of 2D Structure to table

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, DOI: 10.1021/ja042733f

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, DOI: 10.1021/jo991393r

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, DOI:10.1016/S0040-4020(01)00591-9

It:Amphidinolide T1

2006-10-26T13:55:07Z

Ckp05: Addition of large table of data+2D+3D structures

==Introduction: Amphidinolides==

The amphidinolides are a group of very scarce, naturally occurring compounds found in marine microalga dinoflagellates (genus: ''Amphidinium''). These microorganisms live in the inner tissue of the Okinawan flatworm (a Japanese flatworm, genus: ''Amphiscolops'') and take part in a symbiotic relationship with its host. Since the initial discovery of the amphidinolides A-D by Jun’ichi Kobayashi and his co-workers in the 1980’s, further amphidinolides E-Y have been discovered by performing the extraction process on different species of the ''Amphidinium'' genus.<sup>1</sup>

The amphidinolides consist of a highly oxygenated macrolactone of varying ring sizes. Many of the amphidinolides express potent cytotoxicity, which makes them potentially effective anti-cancer fighting compounds, as they would have the ability to attack various cancer cell lines.<sup>2</sup>

The amphidinolide T class has received particular attention since it was discovered in 2000<sup>3</sup>. There are five sub-groups of amphidinolide T: T1, T2, T3, T4 and T5. T1-T5 all contain 7 stereocentres apart from T2, which has 8.<sup>1</sup>

==Amphidinolide T1==

Amphidinolide T1 is extracted from the Y-56 strain of the marine dinoflagellate ''Amphidinium''. Its structure consists of a 19-membered macrolide possessing a tetrahydrofuran ring, an exo-methylene, three branched methyls, a ketone, and a hydroxyl group.<sup>4</sup>

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" |Structure of Amphidinolide T1
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Amphidinolidet1.jpeg|200px|{{PAGENAME}}]]
|-
! {{chembox header}} colspan="3" |3D structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
HEADER NONAME 26-Oct-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 26-Oct-06 0 NONE 4
ATOM 1 O 0 3.111 -2.711 -1.933 0.00 0.00 O+0
ATOM 2 C 0 2.492 -2.100 -0.799 0.00 0.00 C+0
ATOM 3 H 0 1.973 -1.188 -1.108 0.00 0.00 H+0
ATOM 4 C 0 1.474 -3.071 -0.193 0.00 0.00 C+0
ATOM 5 H 0 1.461 -2.962 0.890 0.00 0.00 H+0
ATOM 6 C 0 0.099 -2.795 -0.797 0.00 0.00 C+0
ATOM 7 C 0 -0.880 -2.333 0.253 0.00 0.00 C+0
ATOM 8 C 0 -2.299 -2.840 0.217 0.00 0.00 C+0
ATOM 9 C 0 -3.287 -1.679 0.102 0.00 0.00 C+0
ATOM 10 H 0 -4.085 -1.955 -0.591 0.00 0.00 H+0
ATOM 11 O 0 -2.624 -0.490 -0.397 0.00 0.00 O+0
ATOM 12 C 0 -3.898 -1.391 1.477 0.00 0.00 C+0
ATOM 13 C 0 -4.976 -0.315 1.340 0.00 0.00 C+0
ATOM 14 C 0 -5.587 -0.027 2.713 0.00 0.00 C+0
ATOM 15 C 0 -0.503 -1.503 1.191 0.00 0.00 C+0
ATOM 16 C 0 1.892 -4.507 -0.531 0.00 0.00 C+0
ATOM 17 C 0 3.541 -1.749 0.224 0.00 0.00 C+0
ATOM 18 C 0 4.051 -0.333 0.326 0.00 0.00 C+0
ATOM 19 C 0 2.873 0.613 0.532 0.00 0.00 C+0
ATOM 20 H 0 1.988 0.059 0.835 0.00 0.00 H+0
ATOM 21 O 0 2.607 1.332 -0.687 0.00 0.00 O+0
ATOM 22 C 0 2.755 2.753 -0.426 0.00 0.00 C+0
ATOM 23 H 0 3.115 3.260 -1.315 0.00 0.00 H+0
ATOM 24 C 0 1.431 3.335 0.054 0.00 0.00 C+0
ATOM 25 C 0 0.273 2.551 -0.573 0.00 0.00 C+0
ATOM 26 C 0 -0.976 3.431 -0.617 0.00 0.00 C+0
ATOM 27 C 0 -2.206 2.606 -0.229 0.00 0.00 C+0
ATOM 28 C 0 -2.666 1.764 -1.419 0.00 0.00 C+0
ATOM 29 H 0 -1.802 1.491 -2.027 0.00 0.00 H+0
ATOM 30 C 0 -3.649 2.569 -2.270 0.00 0.00 C+0
ATOM 31 C 0 -3.344 0.507 -0.932 0.00 0.00 C+0
ATOM 32 O 0 -4.546 0.400 -1.038 0.00 0.00 O+0
ATOM 33 C 0 3.839 2.786 0.695 0.00 0.00 C+0
ATOM 34 H 0 4.817 2.491 0.312 0.00 0.00 H+0
ATOM 35 C 0 3.903 4.138 1.402 0.00 0.00 C+0
ATOM 36 C 0 3.225 1.673 1.609 0.00 0.00 C+0
ATOM 37 O 0 3.984 -2.598 0.960 0.00 0.00 O+0
ATOM 38 H 0 3.736 -2.066 -2.292 0.00 0.00 H+0
ATOM 39 H 0 0.190 -2.025 -1.566 0.00 0.00 H+0
ATOM 40 H 0 -0.283 -3.713 -1.255 0.00 0.00 H+0
ATOM 41 H 0 -2.421 -3.508 -0.641 0.00 0.00 H+0
ATOM 42 H 0 -2.501 -3.398 1.137 0.00 0.00 H+0
ATOM 43 H 0 -4.343 -2.303 1.874 0.00 0.00 H+0
ATOM 44 H 0 -3.119 -1.042 2.154 0.00 0.00 H+0
ATOM 45 H 0 -4.531 0.597 0.942 0.00 0.00 H+0
ATOM 46 H 0 -5.755 -0.664 0.662 0.00 0.00 H+0
ATOM 47 H 0 -6.032 -0.939 3.111 0.00 0.00 H+0
ATOM 48 H 0 -4.808 0.323 3.391 0.00 0.00 H+0
ATOM 49 H 0 -6.355 0.740 2.616 0.00 0.00 H+0
ATOM 50 H 0 0.516 -1.144 1.217 0.00 0.00 H+0
ATOM 51 H 0 -1.210 -1.177 1.940 0.00 0.00 H+0
ATOM 52 H 0 2.881 -4.705 -0.117 0.00 0.00 H+0
ATOM 53 H 0 1.172 -5.205 -0.104 0.00 0.00 H+0
ATOM 54 H 0 1.920 -4.631 -1.614 0.00 0.00 H+0
ATOM 55 H 0 4.737 -0.256 1.170 0.00 0.00 H+0
ATOM 56 H 0 4.581 -0.066 -0.590 0.00 0.00 H+0
ATOM 57 H 0 1.353 3.267 1.138 0.00 0.00 H+0
ATOM 58 H 0 1.359 4.381 -0.254 0.00 0.00 H+0
ATOM 59 H 0 0.546 2.255 -1.586 0.00 0.00 H+0
ATOM 60 H 0 0.072 1.659 0.021 0.00 0.00 H+0
ATOM 61 H 0 -0.858 4.256 0.088 0.00 0.00 H+0
ATOM 62 H 0 -1.102 3.833 -1.623 0.00 0.00 H+0
ATOM 63 H 0 -1.953 1.953 0.608 0.00 0.00 H+0
ATOM 64 H 0 -3.012 3.280 0.071 0.00 0.00 H+0
ATOM 65 H 0 -3.159 3.473 -2.634 0.00 0.00 H+0
ATOM 66 H 0 -3.974 1.967 -3.118 0.00 0.00 H+0
ATOM 67 H 0 -4.513 2.843 -1.666 0.00 0.00 H+0
ATOM 68 H 0 2.938 4.355 1.860 0.00 0.00 H+0
ATOM 69 H 0 4.673 4.108 2.173 0.00 0.00 H+0
ATOM 70 H 0 4.144 4.916 0.677 0.00 0.00 H+0
ATOM 71 H 0 2.335 2.027 2.125 0.00 0.00 H+0
ATOM 72 H 0 3.966 1.289 2.309 0.00 0.00 H+0
CONECT 1 2 38 0 0 NONE 77
CONECT 2 1 3 4 17 NONE 78
CONECT 4 2 5 6 16 NONE 79
CONECT 6 4 7 39 40 NONE 80
CONECT 7 6 8 15 0 NONE 81
CONECT 8 7 9 41 42 NONE 82
CONECT 9 8 10 11 12 NONE 83
CONECT 11 9 31 0 0 NONE 84
CONECT 12 9 13 43 44 NONE 85
CONECT 13 12 14 45 46 NONE 86
CONECT 14 13 47 48 49 NONE 87
CONECT 15 7 50 51 0 NONE 88
CONECT 16 4 52 53 54 NONE 89
CONECT 17 2 18 37 0 NONE 90
CONECT 18 17 19 55 56 NONE 91
CONECT 19 18 36 20 21 NONE 92
CONECT 21 19 22 0 0 NONE 93
CONECT 22 21 23 24 33 NONE 94
CONECT 24 22 25 57 58 NONE 95
CONECT 25 24 26 59 60 NONE 96
CONECT 26 25 27 61 62 NONE 97
CONECT 27 26 28 63 64 NONE 98
CONECT 28 27 29 30 31 NONE 99
CONECT 30 28 65 66 67 NONE 100
CONECT 31 28 11 32 0 NONE 101
CONECT 32 31 0 0 0 NONE 102
CONECT 33 22 34 35 36 NONE 103
CONECT 35 33 68 69 70 NONE 104
CONECT 36 33 19 71 72 NONE 105
CONECT 37 17 0 0 0 NONE 106
END NONE 107
END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Properties
|-
| colspan="1" |Chemical Name
| colspan="2"|(+)-amphidinolide T1
|-
| colspan="1" |Auto name/|[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2" | 14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxa-bicyclo[15.2.1]eicosane-7,15-dione
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" | C<sub>25</sub>H<sub>42</sub>O<sub>5</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |O[C@@H]([C@@H](CC(C[C@H](O2)CCC)=C)C)C(C[C@]1([H])O[C@@]([H])(CCCC[C@H](C)C2=O)[C@@H](C)C1)=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 422.60 g/mol
|-
| colspan="1" Beilstein Registry number
| colspan="2" | 8521136
|-
|colspan="1" |Type of Substance
| colspan="2" | heterocyclic
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Physical Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| colspan="2" |63-66°C
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| colspan="2" |
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K'') 
| colspan="2" |
|-
! {{chembox header}} colspan="3"| Crystal Phase
|-
| [http://en.wikipedia.org/wiki/Crystal_system Crystal System]
| colspan="2"|monoclinic
|-
| Crystal Density
| colspan="2" |1.147g/cm3
|-
| [http://en.wikipedia.org/wiki/Temperature Temperature]
| colspan="2" |-160C
|-
! {{chembox header}} colspan="3" | Hazards 
|-
| Main [http://en.wikipedia.org/wiki/Worker_safety_and_health hazard]s
| colspan="2" |cytotoxicity
|-
! {{chembox header}} colspan="3" | Analytical data
|-
| Spectral data
| colspan="2" | [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} colspan="3" | Related compounds
|-
| Amphidinolide T2, Amphidinolide T3, Amphidinolide T4 & Amphidinolide T5
| colspan="2" |
|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 °C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

==References==

1. Elizabeth A. Colby, Timothy F. Jamison, ''A comparative analysis of the total syntheses of the amphidinolide T natural products'', ''Org. Biomol. Chem.'', 2005, '''3''', 2675-2684

2. Elizabeth A. Colby, Karen C. O'Brien, and Timothy F. Jamison, ''Total Syntheses of Amphidinolides T1 and T4 via Catalytic, Stereoselective, Reductive Macrocyclizations'', ''J. Am. Chem. Soc.'', 2005, '''127''', 4297 – 4307, DOI: 10.1021/ja042733f

3. Masashi Tsuda, Tetsuya Endo, and Jun'ichi Kobayashi, Amphidinolide T, ''Novel 19-Membered Macrolide from Marine Dinoflagellate Amphidinium sp.'', ''J. Org. Chem.'', 2000, '''65''', 1349 – 1352, DOI: 10.1021/jo991393r

4. Takaaki Kubota, Tetsuya Endo, Masashi Tsuda, Motoo Shiro and Jun'ichi Kobayashi, ''Amphidinolide T5, a new 19-membered macrolide from a dinoflagellate and X-ray structure of amphidinolide T1'', ''Tetrahedron'', 2001, '''57''', 6175-6179, DOI:10.1016/S0040-4020(01)00591-9

File:Amphidinolidet1.jpg

2006-10-26T13:31:56Z

Ckp05: 2D Structure of amphidinolide T1

2D Structure of amphidinolide T1