Synthesis of the dodecasaccharide fragment representing the O-polysaccharide of Vibrio cholerae O:1, serotype Ogawa, bearing an aglycon offering flexibility for chemical linking to proteins.
Two azidohexasaccharide building blocks, of which the glycosyl acceptor was the 5-(methoxycarbonyl)pentyl glycoside, were coupled using the trichloroacetimidate technology. The 12 azido functions present in the dodecasaccharide thus formed were then converted to amino groups using hydrogen sulfide as a reducing reagent. Subsequent N-acylation with 4-O-benzyl-L-glycero-tetronic acid, followed by catalytic debenzylation yielded the desired spacer-equipped, title dodecasaccharide.
Ogawa
Y
Y
NIDDK, National Institutes of Health, Bethesda, Maryland 20892-0815, USA.
Kovac
P
P
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012703:Serotyping; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014734:Vibrio cholerae / Q000737:chemistry* / Q000276:immunology
D019081:O Antigens; D009844:Oligosaccharides