Structures and comparative characterization of biosynthetic gene clusters for cyanosporasides, enediyne-derived natural products from marine actinomycetes

Amy L. Lane, Sang Jip Nam, Takashi Fukuda, Kazuya Yamanaka, Christopher A. Kauffman, Paul R. Jensen, William Fenical, Bradley S. Moore

Research output: Contribution to journalArticlepeer-review

57 Scopus citations

Abstract

Cyanosporasides are marine bacterial natural products containing a chlorinated cyclopenta[a]indene core of suspected enediyne polyketide biosynthetic origin. Herein, we report the isolation and characterization of novel cyanosporasides C-F (3-6) from the marine actinomycetes Salinispora pacifica CNS-143 and Streptomyces sp. CNT-179, highlighted by the unprecedented C-2′ N-acetylcysteamine functionalized hexose group of 6. Cloning, sequencing, and mutagenesis of homologous ∼50 kb cyanosporaside biosynthetic gene clusters from both bacteria afforded the first genetic evidence supporting cyanosporaside's enediyne, and thereby p-benzyne biradical, biosynthetic origin and revealed the molecular basis for nitrile and glycosyl functionalization. This study provides new opportunities for bioengineering of enediyne derivatives and expands the structural diversity afforded by enediyne gene clusters.

Original languageEnglish
Pages (from-to)4171-4174
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number11
DOIs
StatePublished - 20 Mar 2013

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