<i>C</i>‐Glycosidic UDP‐GlcNAc Analogues as Inhibitors of UDP‐GlcNAc 2‐Epimerase

Abstract

Abstract The first step in the biosynthesis of neuraminic acid, the “epimerisation” of UDP‐GlcNAc to ManNAc, is catalyzed by UDP‐GlcNAc 2‐epimerase. In this paper we report the synthesis of the C ‐glycosidic UDP‐GlcNAc analogues 1 − 5 as substrate‐based inhibitors of this enzyme. The focus is on the optimal distance and geometry of the connection between the sugar and the UDP‐moiety, which are both important for recognition by UDP‐GlcNAc 2‐epimerase. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)