The phenolic mycoside of Mycobacterium ulcerans: structure and taxonomic implications.
Mycobacterium ulcerans and some pathogenic mycobacterial species elaborate wax A consisting of related long-chain beta-diol components (phthiocerol and related compounds) esterified by multimethyl-branched fatty acids. With the exception of M. ulcerans, wax A-containing mycobacteria also synthesize glycosylated phenol phthiocerol diester and related compounds: the so-called phenolic mycosides. In a deliberate effort to characterize this latter class of compounds in M. ulcerans, 20 strains were examined. Phenolic mycosides were found in two strains. Application of chemical analyses, including one- and two-dimensional NMR spectroscopy, allowed the structural elucidation of glycolipids identified as 3-O-methyl-alpha-L-rhamnosyl phenol phthiocerol diphthioceranate investigators. As phenolic mycosides are highly species-specific molecules, this finding stresses the close phylogenetic link between M. marinum and M. ulcerans. Incidentally, a survey of the mycolate content of M. ulcerans showed that methoxymycolate could not be detected in three strains.
Daffé
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Centre de Recherche de Biochimie et de Génétique Cellulaires du CNRS, Toulouse, France.
Varnerot
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Lévy-Frébault
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VV
D005227:Fatty Acids / Q000032:analysis; D006017:Glycolipids / Q000032:analysis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000737:chemistry* / Q000145:classification; D009171:Mycolic Acids / Q000032:analysis; D009170:Nontuberculous Mycobacteria / Q000737:chemistry; D012210:Rhamnose / Q000032:analysis; D013045:Species Specificity
D005227:Fatty Acids; D006017:Glycolipids; D009171:Mycolic Acids; C060732:mycoside G; D012210:Rhamnose