Synthesis of sulfonamide-conjugated glycosyl-amino acid building blocks
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Bornaghi, Laurent F
Poulsen, Sally-Ann
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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