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Journal Article

Biosynthesis of iso-fatty acids in myxobacteria

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Dickschat, J., Bode, H. B., Kroppenstedt, R., Muller, R., & Schulz, S. (2005). Biosynthesis of iso-fatty acids in myxobacteria. ORGANIC & BIOMOLECULAR CHEMISTRY, 3(15), 2824-2831. doi:10.1039/b504889c.

Cite as: https://hdl.handle.net/21.11116/0000-000A-094E-6
The fatty acid (FA) profiles of the myxobacteria Stigmatella aurantiaca and Myxococcus xanthus were investigated by acidic methanolysis of total cell extracts and GC or GC-MS analysis. The main components were 13-methyltetradecanoic acid (iso-15:0) and (Z)-hexadec-11-enoic acid ( 16: 1, omega-5 cis). The biosynthesis of iso-FAs was investigated in several feeding experiments. Feeding of isovaleric acid (IVA) to a mutant impaired in the degradation of leucine to isovaleryl-CoA (IV-CoA) (bkd mutant) of M. xanthus only increased the amount of iso-odd FAs, whereas feeding of isobutyric acid ( IBA) gave increased amounts only of iso-even FAs. In contrast, a bkd mutant of S. aurantiaca gave increased amounts of iso-odd and iso-even fatty acids in both experiments. We assumed that in S. aurantiaca alpha-oxidation takes place. [D-7]-15-Methylhexadecanoic acid ( 8) was synthesised and fed to S. aurantiaca as well as [D-10] leucine and [D-8] valine to elucidate this pathway in more detail. The iso- fatty acid 8 was degraded by alpha- and beta-oxidation steps. [D-10] Leucine was strongly incorporated into iso-odd and iso-even fatty acids, whereas the incorporation rates for [D-8] valine into both types of fatty acids were low. Thus alpha-oxidation plays an important role in the biosynthesis of iso-fatty acids in S. aurantiaca. The incorporation rates observed after feeding of [D-10] leucine and [D-8] valine are the highest for iso-17: 0 compared to the other acids. This indicates the central role of iso-17 : 0 in the biosynthesis of iso-FAs. The shorter homologues seem to be formed mainly by alpha-oxidation and beta-oxidation of this acid. After feeding of 8 traces of unsaturated counterparts of this labelled FA occurred in the extracts indicating that desaturases are active in the biosynthesis of unsaturated fatty acids in S. aurantiaca.