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Biosynthesis of Volatiles by the Myxobacterium Myxococcus xanthus
Author(s) -
Dickschat Jeroen S.,
Wenzel Silke C.,
Bode Helge B.,
Müller Rolf,
Schulz Stefan
Publication year - 2004
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200300813
Subject(s) - biosynthesis , myxococcus xanthus , polyketide , mutant , strain (injury) , malonate , chemistry , biochemistry , decarboxylation , stereochemistry , biology , gene , anatomy , catalysis
Abstract The volatiles emitted from cell cultures of myxobacterium Myxococcus xanthus were collected by use of a closed‐loop stripping apparatus (CLSA) and analyzed by GC‐MS. Two new natural products, ( S )‐9‐methyldecan‐3‐ol (( S )‐ 1 ) and 9‐methyldecan‐3‐one ( 2 ), were identified and synthesized, together with other aliphatic ketones and alcohols, and terpenes. Biosynthesis of the two main components ( S )‐ 1 and 2 was examined in feeding experiments carried out with the wild‐type strain DK1622 and two mutant strains JD300 and DK11017, which are impaired in the degradation pathway from leucine to isovaleryl‐SCoA. Isovaleryl‐SCoA is used as a starter, followed by chain elongation with two malonate units. Subsequent use of methyl malonate and decarboxylation leads to ( S )‐ 1 and 2 . Furthermore, 3,3‐dimethylacrylic acid (DMAA) can be used by the mutant strain to form isovaleryl‐SCoA, which corroborates recent data on the detection of a novel variety of the mevalonate pathway giving rise to isovaleryl‐SCoA from HMGCoA.