Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks

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Lopez, Marie
Bornaghi, Laurent F
Poulsen, Sally-Ann
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2014
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Abstract

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 a-amino group of amino acid precursors or the sidechain e-amino group of lysine precursors.

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Carbohydrate Research

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386

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© 2014 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version

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Medicinal and biomolecular chemistry

Biologically active molecules

Organic chemistry

Biochemistry and cell biology

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