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Biosynthesis of Pseudomonas-Derived Butenolides.

ABSTRACT: Butenolides are well-known signaling molecules in Gram-positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram-negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide?A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas-derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.

SUBMITTER: Klapper M

PROVIDER: S-EPMC7154651 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Biosynthesis of Pseudomonas-Derived Butenolides.

Klapper Martin M Schlabach Kevin K Paschold André A Zhang Shuaibing S Chowdhury Somak S Menzel Klaus-Dieter KD Rosenbaum Miriam A MA Stallforth Pierre P

Angewandte Chemie (International ed. in English) 20200129 14

Butenolides are well-known signaling molecules in Gram-positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram-negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagen ...[more]

PMID: 31880848

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