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Issue 7, 2019
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Synthesis of the β-linked GalNAc-Kdo disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01

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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

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Article information


Submitted
20 Sep 2018
Accepted
12 Oct 2018
First published
12 Oct 2018

Org. Biomol. Chem., 2019,17, 1694-1697
Article type
Communication

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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