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

Title
Structures and comparative characterization of biosynthetic gene clusters for cyanosporasides, enediyne-derived natural products from marine actinomycetes
Authors
Lane A.L.Nam S.-J.Fukuda T.Yamanaka K.Kauffman C.A.Jensen P.R.Fenical W.Moore B.S.
Ewha Authors
남상집
SCOPUS Author ID
남상집scopus
Issue Date
2013
Journal Title
Journal of the American Chemical Society
ISSN
0002-7863JCR Link
Citation
vol. 135, no. 11, pp. 4171 - 4174
Indexed
SCI; SCIE; SCOPUS scopus
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. © 2013 American Chemical Society.
DOI
10.1021/ja311065v
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자연과학대학 > 화학·나노과학전공 > Journal papers
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