Synthesis of eight glycosides of hexasaccharide fragments representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba and Ogawa, bearing aglycons suitable for linking to proteins.
The title substances were prepared from intermediate, fully acetylated alpha-trimethylsilylethyl (SE) glycosides. The latter were assembled in a blockwise manner, using as the glycosyl donor the alpha-glycosyl chloride of a disaccharide bearing two 4-azido-4-deoxy functions. Next, the azido groups in the assembled hexasaccharides were converted to the corresponding amines, and these were acylated with 4-O-benzyl-3-deoxy-L-glycero-tetronic acid in the presence of a water-soluble carbodiimide. The SE glycosides were then transformed to glycosyl imidates, and these were coupled with methyl 6-hydroxyhexanoate or methyl 2-(2-hydroxyethylthio) propionate. The aglycons in the glycosides thus obtained were then converted to the corresponding carboxylic acids or acyl hydrazides. Such compounds are suitable for linking to proteins to obtain neoglycoproteins.
Ogawa
Y
Y
NIDDK, National Institutes of Health, Bethesda, MD 20892-0815, USA.
Lei
P S
PS
Kovác
P
P
D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D019081:O Antigens / Q000138:chemical synthesis / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011135:Polysaccharides, Bacterial / Q000737:chemistry; D012703:Serotyping; D014734:Vibrio cholerae / Q000737:chemistry*
D006001:Glycoconjugates; D006027:Glycosides; D019081:O Antigens; D009844:Oligosaccharides; D011135:Polysaccharides, Bacterial