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.