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

✍ Scribed by Ping-sheng Lei; Yuji Ogawa; Judith L. Flippen-Anderson; Pavol Kováĉ

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 636 KB
• Volume: 275
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00147-l

✦ Synopsis

Methyl 4-azido-4,6-dideoxy-3-O-benzyl-ct-D-mannopyranoside and its analogous 3-O-(4methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were convetted into methyl 4-amino-4,6-dideoxy-2-O-methyl-a-o-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-Lglycero-tetronamido)-2-O-methyl-a-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 Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 5. For Part 4, see ref. [1].