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001-es BibID:	BIBFORM008742
Első szerző:	Chrysina, Evangelia D.
Cím:	Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case / Evangelia D. Chrysina, Éva Bokor, Kyra-Melinda Alexacou, Maria-Despoina Charavgi, George N. Oikonomakos, Spyros E. Zographos, Demetres D. Leonidas, Nikos G. Oikonomakos, László Somsák
Dátum:	2009
Megjegyzések:	Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplén method furnished beta-D-Glcp-NHCO-R derivatives as well as 1-(beta-D-Glcp)-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:	Tetrahedron: Asymmetry. - 20 : 6-8 (2009), p. 733-740. -
További szerzők:	Bokor Éva (1982-) (vegyész) Alexacou, Kyra-Melinda Charavgi, Maria-Despoina Oikonomakos, George N. Zographos, Spyros E. Leonidas, Demetres D. Oikonomakos, Nikos G. Somsák László (1954-) (vegyész)
Internet cím:	DOI elektronikus változat
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