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.
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.
Lei
P S
PS
NIDDK, National Institutes of Health, Bethesda, MD 20892, USA.
Ogawa
Y
Y
Flippen-Anderson
J L
JL
Kovác
P
P
D000942:Antigens, Bacterial / Q000737:chemistry; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D000939:Epitopes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D019081:O Antigens / Q000737:chemistry* / Q000276:immunology; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D012703:Serotyping; D014734:Vibrio cholerae / Q000737:chemistry* / Q000276:immunology
D000942:Antigens, Bacterial; D000939:Epitopes; D019081:O Antigens; C096652:methyl 4,6-dideoxy-4-(3-deoxy-glycero-tetronamido)-2-O-methylmannopyranoside; D012210:Rhamnose