Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks

• An efficient synthesis of glycoconjugate amino acid building blocks is reported.
• The method provides novel sulfonamide-linked glycoconjugates.
• The method is compatible with a range of amino acids.
• The method opens new possibilities for the synthesis of glycopeptide mimetics.

The efficient synthesis of novel glycoconjugate amino acid building blocks wherein the amino acid and carbohydrate moieties are linked via a sulfonamide functional group is reported. The general reaction sequence consists of coupling a glycosyl thioacetate to an amino acid methyl ester followed by oxidation and deprotection of the carbohydrate moiety. We demonstrate the synthesis of derivatives from a range of amino acids, with reaction at either the α-amino group of amino acid precursors or the sidechain ε-amino group of lysine precursors.

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