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Volume 159, Issue Pt_1

Structural elucidation and genomic scrutiny of the C–C mycolic acids of Free

Abstract

Mycolic acids, very long-chain α-alkyl, β-hydroxylated fatty acids, occur in the members of the order where their chain lengths (C–C) and structural features (oxygen functions, or double bonds, cyclopropane rings and methyl branches) are genus- and species-specific. The molecular composition and structures of the mycolic acids of two species belonging to the genus were determined by a combination of modern analytical chemical techniques, which include MS and NMR. They consist of mono-ethylenic CC (α′), di-ethylenic C–C (α) and extremely long-chain mycolic acids (α) ranging from 92 to 98 carbon atoms and containing three unsaturations, and/or double bonds and/or cyclopropanes. The double bonds in each class of mycolic acids were positioned by oxidative cleavage and exhibit locations similar to those of α- and α′-mycolic acids of mycobacteria. For the ultralong chain α-mycolic acids, the three double bonds were located at equally spaced carbon intervals (C–C), with the methyl branches adjacent to the proximal and distal double bonds. Examination of the genome compared with those of other members of the indicated two obvious differences in genes encoding the elongation fatty acid (FAS-II) enzymes involved in the biosynthesis of mycolic acids: the organization of 3-ketoacyl-ACP synthases (KasA and KasB) and (3)-hydroxyacyl-ACP dehydratases (HadAB/BC), on one hand, and the presence of two copies of the gene encoding the catalytic domain of the latter enzyme type, on the other. This observation is discussed in light of the most recent data accumulated on the biosynthesis of this hallmark of .

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2013-01-01
2024-04-24
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Structural elucidation and genomic scrutiny of the C60–C100 mycolic acids of Segniliparus rotundus
Microbiology 159, 191 (2013); https://doi.org/10.1099/mic.0.063479-0
/content/journal/micro/10.1099/mic.0.063479-0
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