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Biosynthesis of Pseudomonas ‐Derived Butenolides
Author(s) -
Klapper Martin,
Schlabach Kevin,
Paschold André,
Zhang Shuaibing,
Chowdhury Somak,
Menzel KlausDieter,
Rosenbaum Miriam A.,
Stallforth Pierre
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201914154
Subject(s) - gene cluster , biology , pseudomonas , transposable element , transposon mutagenesis , gene , genetics , heterologous expression , homology (biology) , mutagenesis , bacteria , computational biology , mutant , recombinant dna
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.