6533b7dafe1ef96bd126eaab

RESEARCH PRODUCT

ChemInform Abstract: Synthetic O-Glycopeptides as Model Substrates for Glycosyltransferases.

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Abstract A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives as acceptors. The urethane group is easily exchanged for the natural N-acetyl moiety and O-deacetylation is achieved with hydrazine/methanol. The resulting O-GlcNAc derivatives are subjected to an enzymatic galactosylation procedure using β-1,4-galactosyltransferase (EC 2.4.1.22) to furnish O-glycopeptides of the neolactosamine type.