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Title: Synthesis and crystal structure of methyl 4-6-dideoxy-4-(3-deoxy-L- glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, the methyl alpha-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa. Author: Lei PS, Ogawa Y, Flippen-Anderson JL, Kovác P. Journal: Carbohydr Res; 1995 Sep 15; 275(1):117-29. PubMed ID: 7585718. Abstract: Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D- mannopyranoside [sequence: see text]. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero- tetronamido)-2-methyl-alpha-D-mannopyranose [sequence: see text], the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-O- methyl-4-trifluoroacetamido-alpha-D-mannopyranoside [sequence: see text] is also described.[Abstract] [Full Text] [Related] [New Search]