Help Privacy Policy Disclaimer
  Advanced SearchBrowse




Journal Article

Biosynthesis and identification of volatiles released by the myxobacterium Stigmatella aurantiaca

There are no MPG-Authors in the publication available
External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available

Dickschat, J., Bode, H. B., Wenzel, S., Muller, R., & Schulz, S. (2005). Biosynthesis and identification of volatiles released by the myxobacterium Stigmatella aurantiaca. CHEMBIOCHEM, 6(11), 2023-2033. doi:10.1002/cbic.200500174.

Cite as: https://hdl.handle.net/21.11116/0000-000A-0954-E
The volatiles released by agar plate cultures of two strains of the myxobacterium Stigmatella aurantiaca (strains Sg a 15 and DW4/3-1) were collected in a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Large numbers of substances from different compound classes (ketones, esters, lactones, terpenes, and sulfur and nitrogen compounds) were identified; several of them are reported from natural sources for the first time. The volatiles 2-methyltridecan-4-one (17), its isomer 3-methyltridecan-4-one (20), and the higher homologue 2-methyltetradecan-4-one (18) were identified in the extracts of both strains and were synthesized. In addition, strain Sg a 75 produced 2,12-dimethyltridecan4-one (79), 2-methyltridec-2-en-4-one (2 3), and a series of phenyl ketones, among them 1-phenyldecan-1-one (14) and 9-methyl-1-phenyldecan-1-one (16), whereas strain DW4/3-1 emitted traces of 10-methylundecan-2-one (21). The biosynthesis of 14 and 16 was examined in feeding experiments with deuterated precursors carried out on agar plate cultures. The leucine-derived starter unit isovalerate was shown to be incorporated into 16, as was phenylalanine-derived benzoic acid into both 14 and 16. The results point to formation both of the phenyl ketones and of the structurally related aliphatic ketones through an unusual head-to-head coupling between a starter unit such as benzoyl-CoA and a forty acyl-CoA, followed by decarboxylation.