Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

Article abstract of DOI:10.1016/0008-6215(95)00147-L

Methyl 4-azido-4,6-dideoxy-3-O-benzyl-α-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-α-D-mannopyranoside.Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetranamido)-2-O-methyl-α-D-mannopyranose, 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-α-D-mannopyranoside is also described.Keywords: O-Polysaccharide; Vibrio cholerae O:1, serotype Ogawa; α-D-Mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-teronamido)-2-O-methyl; Synthesis; Antigenic determinant