Affordable Access

Synthesis of 1,2,3-triazoles from xylosyl and 5-thioxylosyl azides : evaluation of the xylose scaffold for the design of potential glycogen phosphorylase inhibitors

Authors
  • Goyard, D
  • Baron, M
  • Skourti, PV
  • Chajistamatiou, AS
  • Docsa, T
  • Gergely, P
  • Chrysina, ED
  • Praly, JP
  • Vidal, S.
Publication Date
Oct 05, 2012
Source
HAL-INRIA
Keywords
License
Unknown
External links

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.

Report this publication

Statistics

Seen <100 times