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Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic Probes for glycosyltransferases

Authors
Journal
Bioorganic & Medicinal Chemistry
0968-0896
Publisher
Elsevier
Publication Date
Volume
8
Issue
8
Identifiers
DOI: 10.1016/s0968-0896(00)00139-5

Abstract

Abstract An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Selectfluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed, and the fluorinated sugar nucleotides have been used as probes for glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nucleotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase.

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