Absolute configuration of the unique 2,6-dideoxy-4-O-methyl-arabino-hexopyranose of the major phenolic glycolipid antigen from Mycobacterium kansasii.
The antigenicity and the structure of the major phenolic glycolipid from Mycobacterium kansasii have been established. A monoacetylated tetrasaccharide structure was proposed for the oligosaccharide moiety in which the distal sugar, unique in nature, corresponds to 2,6-dideoxy-4-O-methyl-alpha-arabinohexopyranose. Its terminal position in the oligosaccharide part confers to this residue a key role in the antigen-antibody interaction. By improvement of the methanolysis procedure, this new kind of sugar was obtained in higher amounts than by hydrolysis of the glycolipid. Its 1H-NMR spectrum is presented and its optical rotatory power measurement agrees with a D absolute configuration while the deoxyhexoses involved in the glycolipid tetrasaccharide structure present the L absolute configuration.
Fournie
J J
JJ
Centre de Recherche de Biochimie et de Génétique Cellulaires, Centre National de la Recherche Scientifique, Toulouse, France.
Riviere
M
M
Puzo
G
G
D000937:Antigen-Antibody Reactions; D000942:Antigens, Bacterial / Q000032:analysis*; D002241:Carbohydrates / Q000032:analysis; D006017:Glycolipids / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000276:immunology*; D009170:Nontuberculous Mycobacteria / Q000276:immunology*; D010636:Phenols / Q000032:analysis*; D011135:Polysaccharides, Bacterial / Q000032:analysis* / Q000502:physiology; D013329:Structure-Activity Relationship
D000942:Antigens, Bacterial; D002241:Carbohydrates; D006017:Glycolipids; D010636:Phenols; D011135:Polysaccharides, Bacterial