Sulfonium Acids Loaded onto an Unusual Thiotemplate Assembly Line Construct the Cyclopropanol Warhead of a Burkholderia Virulence Factor

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Abstract: Pathogenic bacteria of the Burkholderia pseudomallei group cause severe infectious diseases such as glanders and melioidosis. Malleicyprols were identified as important bacterial virulence factors, yet the biosynthetic origin of their cyclopropanol warhead has remained enigmatic. By a combination of mutational analysis and metabolomics we found that sulfonium acids, dimethylsulfoniumpropionate (DMSP) and gonyol, known as osmolytes and as crucial components in the global organosulfur cycle, are key intermediates en route to the cyclopropanol unit. Functional genetics and in vitro analyses uncover a specialized pathway to DMSP involving a rare prokaryotic SET‐domain methyltransferase for a cryptic methylation, and show that DMSP is loaded onto the NRPS‐PKS hybrid assembly line by an adenylation domain dedicated to zwitterionic starter units. Then, the megasynthase transforms DMSP into gonyol, as demonstrated by heterologous pathway reconstitution in E. coli.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Sulfonium Acids Loaded onto an Unusual Thiotemplate Assembly Line Construct the Cyclopropanol Warhead of a Burkholderia Virulence Factor ; volume:132 ; number:32 ; year:2020 ; pages:13613-13617 ; extent:5
Angewandte Chemie ; 132, Heft 32 (2020), 13613-13617 (gesamt 5)

Creator: Trottmann, Felix
Ishida, Keishi
Franke, Jakob
Stanišić, Aleksa
Ishida‐Ito, Mie
Kries, Hajo
Pohnert, Georg
Hertweck, Christian

DOI: 10.1002/ange.202003958

URN: urn:nbn:de:101:1-2022052912512846614362

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:26 AM CEST

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Associated

Trottmann, Felix
Ishida, Keishi
Franke, Jakob
Stanišić, Aleksa
Ishida‐Ito, Mie
Kries, Hajo
Pohnert, Georg
Hertweck, Christian

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