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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.
Goyard, David; Baron, Marc; Skourti, Paraskevi V; Chajistamatiou, Aikaterini S; Docsa, Tibor; Gergely, Pál; Chrysina, Evangelia D; Praly, Jean-Pierre; Vidal, Sébastien.
Afiliación
  • Goyard D; Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique 2, Glycochimie, UMR 5246, CNRS, Université Claude Bernard Lyon 1, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
Carbohydr Res ; 364: 28-40, 2012 Dec 15.
Article en En | MEDLINE | ID: mdl-23147043
Various acetylenic derivatives and acetylated ß-D-xylopyranosyl azide or the 5-thio-ß-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.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Triazoles / Xilosa / Glucógeno Fosforilasa / Inhibidores Enzimáticos Idioma: En Revista: Carbohydr Res Año: 2012 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Países Bajos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Triazoles / Xilosa / Glucógeno Fosforilasa / Inhibidores Enzimáticos Idioma: En Revista: Carbohydr Res Año: 2012 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Países Bajos