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.
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.
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