Synthesis of the β-linked GalNAc-Kdo disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01

Abstract

The first construction of the challenging β-(1 → 5)-linked GalNAc-Kdo skeleton is described for the synthesis of the disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01. TfOH-catalyzed glycosylation of N-Troc-protected D-galactosaminyl N-phenyl trifluoroacetimidate with a sterically hindered 5-hydroxyl group of the β-Kdo building block in toluene proceeded smoothly to provide the desired disaccharide in excellent yield with satisfactory β-selectivity. An optimal sequence for the deprotection of the disaccharide skeleton was found to access the disaccharide antigen of Kingella kingae KK01 for further immunological studies.