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Synthesis and biological evaluation of the [d-MeAla(11)]-epimer of coibamide A.

Abstract：

:Coibamide A is a highly potent antiproliferative cyclic depsipeptide, which was originally isolated from a Panamanian marine cyanobacterium. In this study, the synthesis of coibamide A has been investigated using Fmoc-based solid-phase peptide synthesis followed by the cleavage of the resulting linear peptide from the resin and its subsequent macrolactonization. The peptide sequence of the linear coibamide A precursor was constructed on a solid-support following the optimization of the coupling conditions, where numerous coupling agents were evaluated. The macrocyclization of the resulting linear peptide provided the [d-MeAla(11)]-epimer of coibamide A, which exhibited nanomolar cytotoxic activity towards a number of human cancer cell lines.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Nabika R,Suyama TL,Hau AM,Misu R,Ohno H,Ishmael JE,McPhail KL,Oishi S,Fujii N

doi

10.1016/j.bmcl.2014.11.044

subject

Has Abstract

pub_date

2015-01-15 00:00:00

pages

302-6

issue

2

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(14)01228-1

journal_volume

25

pub_type

杂志文章

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