Coibamide A

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Coibamide A
Coibamide A.svg
Names
IUPAC name
[(2S)-1-[[(2S)-1-[[(2S)-1-[[(3S,6S,9S,12S,15S,18S,21S,22R)-15-[(2S)-butan-2-yl]-18-(methoxymethyl)-6-[(4-methoxyphenyl)methyl]-3,4,10,12,16,19,22-heptamethyl-9-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]-methylamino]-4-methyl-1-oxopentan-2-yl]-methylamino]-3-methoxy-1-oxopropan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl] (2S)-2-(dimethylamino)-3-methylbutanoate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C65H110N10O16/c1-26-40(10)52-56(77)66-41(11)57(78)70(17)47(31-36(2)3)55(76)67-46(33-44-27-29-45(89-25)30-28-44)58(79)69(16)42(12)64(85)90-43(13)53(62(83)72(19)50(35-88-24)61(82)74(52)21)75(22)59(80)48(32-37(4)5)71(18)60(81)49(34-87-23)73(20)63(84)54(39(8)9)91-65(86)51(38(6)7)68(14)15/h27-30,36-43,46-54H,26,31-35H2,1-25H3,(H,66,77)(H,67,76)/t40-,41-,42-,43+,46-,47-,48-,49-,50-,51-,52-,53-,54-/m0/s1
    Key: LVHKHLZPRPTQJG-BNLDXBMISA-N
  • CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N([C@H](C(=O)N1C)COC)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](COC)N(C)C(=O)[C@H](C(C)C)OC(=O)[C@H](C(C)C)N(C)C)C)C)C)CC2=CC=C(C=C2)OC)CC(C)C)C)C
Properties
C65H110N10O16
Molar mass 1287.649 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coibamide A is an antiproliferative depsipeptide. It comes from the Leptolyngbya cyanobacterium. [1]

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Valerie J. Paul is the Director of the Smithsonian Marine Station at Fort Pierce, in Fort Pierce, FL since 2002 and the Head Scientist of the Chemical Ecology Program. She is interested in marine chemical ecology, and specializes in researching the ecology and chemistry of Cyanobacteria, blue-green algae, blooms. She has been a fellow of the American Association for the Advancement of Science since 1996, and was the chairperson of the Marine Natural Products Gordon Research Conference in 2000.

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References

  1. Medina, Rebecca A.; Goeger, Douglas E.; Hills, Patrice; Mooberry, Susan L.; Huang, Nelson; Romero, Luz I.; Ortega-Barría, Eduardo; Gerwick, William H.; McPhail, Kerry L. (2008). "Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbyasp". Journal of the American Chemical Society. 130 (20): 6324–5. doi:10.1021/ja801383f. PMC   2659736 . PMID   18444611.