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Coupling of carbohydrate antigens to protein carriers is a typical approach to enhancing the immunogenicity of carbohydrate-based vaccines. Glycoconjugates with well-defined structures are needed for studies defining the structural variables that govern antibody responses. We report a chemical strategy for preparation of an array of glycoconjugates containing saccharides of desired molecular sizes...
Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-α-d-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-d-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O-benzyl-3,4,6-trideoxy-3-fluoro-α-d-altropyranoside...
Derivatives of methyl α-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-l-glycero-tetronic acid with the methyl α-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition...
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