Issue 7, 2019

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
20 sep. 2018
Accepted
12 oct. 2018
First published
12 oct. 2018

Org. Biomol. Chem., 2019,17, 1694-1697

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

L. Zhuang, Y. Chen, Q. Lou and Y. Yang, Org. Biomol. Chem., 2019, 17, 1694 DOI: 10.1039/C8OB02340A

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