Journal
CARBOHYDRATE RESEARCH
Volume 364, Issue -, Pages 28-40Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2012.09.020
Keywords
Xylose; Sulfoxide; Cycloaddition; 1,2,3-Triazole; Glycogen phosphorylase
Funding
- CNRS [4576]
- University Claude Bernard Lyon 1
- French Agence Nationale de la Recherche (ANR) [ANR-08-BLAN-0305]
- Hungarian Science Research Fund [OTKA CNK80709, REGPOT-2008-1-No 230146 'EUROSTRUCT', REGPOT-2009-1-No 245866 'ARCADE']
- Hungarian Academy of Sciences
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Various acetylenic derivatives and acetylated beta-D-xylopyranosyl azide or the 5-thio-beta-D-xylopyranosyl analogue were coupled by Cu(I)-catalyzed azide alkyne 1,3-dipolar cycloaddition (CuAAC) to afford a series of 1-xylosyl-4-substituted 1,2,3-triazoles. Controlled oxidation of the endocyclic sulfur atom of the 5-thioxylose moiety led to the corresponding sulfoxides and sulfones. Deacetylation afforded 19 hydroxylated xylose and 5-thioxylose derivatives, found to be only sparingly water-soluble. Compared to glucose-based analogues, they appeared to be much weaker inhibitors of glycogen phosphorylase, as the absence of a hydroxymethyl group weakens their binding at the enzyme active site. However, such new xylose derivatives might be useful glycomimetics. (C) 2012 Elsevier Ltd. All rights reserved.
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