Chemical synthesis of disaccharides of the specific phenolic glycolipid antigens from Mycobacterium leprae and of related sugars.
O-(3,6-Di-O-methyl-beta-D-glucopyranosyl)-(1----4)-2,3,-di-O-methyl-L -rhamnopyranose, which is the nonreducing disaccharide of the haptenic trisaccharide of the Mycobacterium leprae-specific, phenolic glycolipid I, O-(6-O-methyl-beta-D-glucopyranosyl)-(1----4)-2,3-di-O-methyl-L-rhamn opyranose, the nonreducing end of the specific, phenolic glycolipid III, and the nonhaptenic O-beta-(D-glucopyranosyl)-(1----4)-2,3-di-O-methyl-L-rhamnopyranose++ +, were synthesized in relatively good yield from 3-O-methyl-D-glucose, or D-glucose, and L-rhamnose via Koenigs-Knorr reactions. These disaccharides can be used as precursors in the synthesis of the trisaccharide unit of phenolic glycolipid I and of neoglycoconjugates suitable for the serodiagnosis of leprosy.
D000942:Antigens, Bacterial; D004187:Disaccharides / Q000138:chemical synthesis*; D006017:Glycolipids; D006241:Haptens; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009166:Mycobacterium leprae / Q000276:immunology*; D013329:Structure-Activity Relationship
D000942:Antigens, Bacterial; D004187:Disaccharides; D006017:Glycolipids; D006241:Haptens; D007202:Indicators and Reagents