Abstract
Various acetylenic derivatives and acetylated β-D-xylopyranosyl azide or the 5-thio-β-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.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Alkynes / chemistry
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Biomimetic Materials / chemistry
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Catalytic Domain
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Cycloaddition Reaction / methods
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Enzyme Activation
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Glucosamine / analogs & derivatives
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Glucosamine / chemistry
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Glucose / analogs & derivatives
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Glucose / chemistry
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Glycogen Phosphorylase / antagonists & inhibitors*
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Glycogen Phosphorylase / chemistry
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Glycogen Synthase / chemistry
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Magnetic Resonance Spectroscopy
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Oxidation-Reduction
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Protein Binding
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Solubility
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Stereoisomerism
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Sulfoxides / chemistry
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Triazoles / chemical synthesis*
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Triazoles / chemistry
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Water / chemistry
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Xylose / chemistry*
Substances
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Alkynes
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Enzyme Inhibitors
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Sulfoxides
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Triazoles
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Water
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5-thio-D-glucose
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N-acetylglucopyranosylamine
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Xylose
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Glycogen Phosphorylase
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Glycogen Synthase
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Glucose
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Glucosamine