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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| http://dx.doi.org/10.1016/j.carres.2013.08.017 | DOI Listing |
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