Structure and biosynthesis of the marine streptomycete ansamycin ansalactam A and its distinctive branched chain polyketide extender unit

Micheal C. Wilson, Sang Jip Nam, Tobias A.M. Gulder, Christopher A. Kauffman, Paul R. Jensen, William Fenical, Bradley S. Moore

Research output: Contribution to journalArticlepeer-review

81 Scopus citations

Abstract

Reported is the structure and biosynthesis of ansalactam A, an ansamycin class polyketide produced by an unusual modification of the polyketide pathway. This new metabolite, produced by a marine sediment-derived bacterium of the genus Streptomyces, possesses a novel spiro ?-lactam moiety and a distinctive isobutyryl polyketide fragment observed for the first time in this class of natural products. The structure of ansalactam A was defined by spectroscopic methods including X-ray crystallographic analysis. Biosynthetic studies with stable isotopes further led to the discovery of a new, branched chain polyketide synthase extender unit derived from (E)-4-methyl-2-pentenoic acid for polyketide assembly observed for the first time in this class of natural products.

Original languageEnglish
Pages (from-to)1971-1977
Number of pages7
JournalJournal of the American Chemical Society
Volume133
Issue number6
DOIs
StatePublished - 16 Feb 2011

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