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Methylobacterium extorquens AM1 produces a novel type of acyl‐homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions
Author(s) -
Nieto Penalver Carlos G.,
Morin Danièle,
Cantet Franck,
Saurel Olivier,
Milon Alain,
Vorholt Julia A.
Publication year - 2006
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/j.febslet.2005.12.062
Subject(s) - side chain , homoserine , chemistry , stereochemistry , lactone , double bond , organic chemistry , biochemistry , quorum sensing , gene , virulence , polymer
Acyl‐homoserine lactones (acyl‐HSLs) have emerged as important regulatory molecules for many gram‐negative bacteria. We have found that Methylobacterium extorquens AM1, a member of the pink‐pigmented facultative methylotrophs commonly present on plant surfaces, produces several acyl‐HSLs depending upon the carbon source. A novel HSL was discovered with a double unsaturated carbon chain ( N ‐(tetradecenoyl)) (C14:2) and characterized by MS and proton NMR. This long‐chain acyl‐HSL is synthesized by MlaI that also directs synthesis of C14:1‐HSL. The Alphaproteobacterium also produces N ‐hexanoyl‐HSL (C6‐HSL) and N ‐octanoyl‐HSL (C8‐HSL) via Msa I.