Structures and Comparative Characterization of Biosynthetic Gene Clusters for Cyanosporasides, Enediyne-Derived Natural Products from Marine Actinomycetes

TitleStructures and Comparative Characterization of Biosynthetic Gene Clusters for Cyanosporasides, Enediyne-Derived Natural Products from Marine Actinomycetes
Publication TypeJournal Article
Year of Publication2013
AuthorsLane AL, Nam SJ, Fukuda T, Yamanaka K, Kauffman CA, Jensen PR, Fenical W, Moore BS
JournalJournal of the American Chemical Society
Volume135
Pagination4171-4174
Date Published2013/03
Type of ArticleArticle
ISBN Number0002-7863
Accession NumberWOS:000316774100003
Keywordsinsights; salinispora-tropica
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 similar to 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.

DOI10.1021/ja311065v
Short TitleJ. Am. Chem. Soc.
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