Total Synthesis of Conjugation-Ready Hyperbranched Pentasaccharide of Clavibacter phaseoli VKM Ac-2641T by [Au]/[Ag] Catalysis

Abstract

Infections by Clavibacter spp. cause an economic burden to farmers. The components present in the cell wall glycopolymers (CWGs) are important for studying the host–pathogen interactions, colonization, and infection. A pentasaccharide containing a hyperbranched Ribf-, Galf-, and Manp- has recently been identified. Herein, we describe the first total synthesis of the conjugation-ready hyperbranched pentasaccharide of C. phaseoli VKM Ac-2641T using the [Au]/[Ag]-catalyzed glycosidation chemistry of ethynylcyclohexyl carbonate glycosyl donors. The pentasaccharide was synthesized in a highly convergent fashion from readily accessible monosaccharide building blocks.