Synthesis and evaluation of a C-glycosyl nucleoside as an inhibitor of chitin synthase.
As part of our ongoing program devoted to inhibit chitin synthases, we have prepared a novel C-glycosyl nucleoside as metabolically stable substrate analog of UDP-GlcNAc. The synthetic strategy relies on the consecutive coupling of nucleoside and amino C-glycosyl moieties with L-tartaric acid. However, this compound inhibited only weakly chitin synthase I, with an IC(50) value of 20 mM.
Xie
J
J
Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie, CNRS UMR 7613, 4 Place Jussieu, F-75005 Paris, France. xie@ccr.jussieu.fr
Thellend
A
A
Becker
H
H
Vidal-Cros
A
A
D002687:Chitin Synthase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D003857:Deoxyuridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000031:analogs & derivatives*
D005960:Glucosides; C438305:N-(2-(2'- N-acetylamino-2'-deoxyglucopyranosyl)ethyl)-N'-(5'-deoxyuridin-5'-yl)-2,3-dihydroxysuccinamide; D014537:Uridine Diphosphate N-Acetylglucosamine; D002687:Chitin Synthase; D003857:Deoxyuridine