Biosynthesis of volatiles by the myxobacterium Myxococcus xanthus.
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.
Dickschat
Jeroen S
JS
Technische Universität Braunschweig, Institut für Organische Chemie, Hagenring 30, 38106 Braunschweig, Germany.
Wenzel
Silke C
SC
Bode
Helge B
HB
Müller
Rolf
R
Schulz
Stefan
S
D000179:Acrylates / Q000737:chemistry / Q000378:metabolism; D000214:Acyl Coenzyme A / Q000737:chemistry / Q000378:metabolism; D002478:Cells, Cultured; D003653:Decarboxylation; D007659:Ketones / Q000032:analysis / Q000378:metabolism*; D008314:Malonates / Q000737:chemistry; D013058:Mass Spectrometry; D008798:Mevalonic Acid / Q000737:chemistry / Q000378:metabolism; D016941:Myxococcus xanthus / Q000737:chemistry / Q000378:metabolism*; D000442:Octanols / Q000032:analysis / Q000378:metabolism; D013729:Terpenes / Q000032:analysis / Q000378:metabolism; D014835:Volatilization
D000179:Acrylates; D000214:Acyl Coenzyme A; D007659:Ketones; D008314:Malonates; D000442:Octanols; D013729:Terpenes; C017447:isovaleryl-coenzyme A; C005230:methyl malonate; C036658:acrylic acid; D008798:Mevalonic Acid