期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 14, 期 21, 页码 7293-7301出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2006.06.057
关键词
glycosyl radical; C-glycoside; inhibitor; glycosyltransferase; NDP sugar analogue
A series of C-glycosyl ethylphosphonophosphate analogues of UDP-Glc, UDP-Gal, UDP-GlcNAc and GDP-Fuc were synthesized from the corresponding C-glycosyl ethylphosphonic acids. Analogues were obtained as alpha-anomers through either diastereoselective photo-induced radical addition of glycosyl bromides (D-Glc, D-Gal and L-Fuc) to diethyl vinylphosphonate, or a multi-step sequence (D-GlcNAc), with subsequent coupling with morpholidate-activated nucleotide monophosphates. The in vitro inhibitory activity of UDP-Gal, GDP-Fuc and UDP-GlcNAc analogues towards glycosyltransferases (beta-1,4-Gaff, FUT3 and LgtA) was evaluated through a competition fluorescence assay and IC50 values of 40 mu M, 2 mM and 3.5 mM were obtained, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
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