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Structural elucidation and genomic scrutiny of the C60 to C100 mycolic acids of Segniliparus rotundus.
MedLine Citation:
PMID:  23154972     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Mycolic acids, very long-chain α-alkyl, β-hydroxylated fatty acids, occur in the Corynebacteriales order where their chain lengths (C26 to C88) and structural features (oxygen functions, cis or trans 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 Segniliparus were determined by a combination of modern analytical chemical techniques, which include mass spectrometry and NMR. They consist of mono-ethylenic C62-64 (α'), the di-ethylenic C77-C79 (α) and extremely long-chain mycolic acids (α+) ranging from 92 to 98 carbon atoms and containing three unsaturations, cis and/or trans double bonds and/or cyclopropanes. The double bonds in each class of mycolic acids were positioned by oxidative cleavage and exhibit the locations similar to those of α- and α'-mycolic acids of mycobacteria. For the α+-mycolic acids, the three double bonds were located at equally-spaced carbon intervals (C13 to C16), with the methyl branches adjacent to the proximal and distal trans double bonds. Examination of the Segniliparus rotundus genome in comparison with those of other Corynebacteriales 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 (3R)-hydroxyacyl-ACP dehydratases (HadAB/BC), on one hand, and the presence of two copies of the hadB gene encoding the catalytic domain of the latter enzyme. This observation is discussed in the light of the last data accumulated on the biosynthesis of the hallmark of Corynebacteriales.
Authors:
Marie-Antoinette Lanéelle; Nathalie Eynard; Lucie Spina; Anne Lemassu; Françoise Laval; Emilie Huc; Gilles Etienne; Hedia Marrakchi; Mamadou Daffé
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-15
Journal Detail:
Title:  Microbiology (Reading, England)     Volume:  -     ISSN:  1465-2080     ISO Abbreviation:  Microbiology (Reading, Engl.)     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9430468     Medline TA:  Microbiology     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
IPBS du CNRS - Université de Toulouse (Université Paul Sabatier III).
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