Reliable Chemical Synthesis of UDP-3--[()-3-Hydroxydecanoyl]-GlcNAc: The Native Substrate of LpxC.

Herein, we describe a reliable and efficient approach for the first chemical synthesis of biologically significant and complex 3--(-3-hydroxydecanoyl) modified uridine diphosphate -acetylglucosamine that is the native substrate of LpxC involved in the biosynthesis of the cell wall of . The synthetic protocol provides a successful example for the reliable preparation of modified nucleoside diphosphate sugar, which features judiciously selected protecting groups, the formation of pyrophosphate linkage with 5'-phosphate nucleoside as nucleophile, and the straightforward purification process.