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Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces.

ABSTRACT: Butyrolactol A is an antifungal polyketide of Streptomyces bearing an uncommon tert-butyl starter unit and a polyol system in which eight hydroxy/acyloxy carbons are contiguously connected. Except for its congener butyrolactol B, there exist no structurally related natural products to date. In this study, inspired by our previous genomic analysis, incorporation of ¹³C- and ²H-labeled precursors into butyrolactol A was investigated. Based on the labeling pattern and sequencing analytical data, we confirmed that the tert-butyl group is derived from valine and its C-methylation with methionine and the polyol carbons are derived from a glycolysis intermediate, possibly hydroxymalonyl-ACP.

SUBMITTER: Harunari E

PROVIDER: S-EPMC5355916 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces.

Harunari Enjuro E Komaki Hisayuki H Igarashi Yasuhiro Y

Beilstein journal of organic chemistry 20170308

Butyrolactol A is an antifungal polyketide of Streptomyces bearing an uncommon tert-butyl starter unit and a polyol system in which eight hydroxy/acyloxy carbons are contiguously connected. Except for its congener butyrolactol B, there exist no structurally related natural products to date. In this study, inspired by our previous genomic analysis, incorporation of 13C- and 2H-labeled precursors into butyrolactol A was investigated. Based on the labeling patter ...[more]

PMID: 28382182

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