Synthesis and conformational analysis of neoglycoconjugates derived from O- and S-glucose

Using olefin metathesis as a key step, four neoglycoconjugates incorporating α-O-glucose, α-S-glucose or β-S-glucose as a carbohydrate unit and l-serine or l-cysteine as an amino acid moiety have been synthesized. The four-atom carbon spacer allows the carbohydrate to explore a wide-ranging conformational space, which may have important implications for the molecular recognition of these molecules.

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• The synthesis and the conformational analysis of four novel neoglycopeptides derived from glucose are described.
• These neoglycopeptides incorporate both S- and O-glycosidic linkages.
• The sugar and peptide moieties are linked by a four-atom carbon spacer.
• The linker allows the carbohydrate to explore a wide-ranging conformational space.