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A Highly α-Stereoselective Synthesis of Oligosaccharide Fragments of the Vi Antigen from Salmonella typhi and Their Antigenic Activities

✍ Scribed by Lin Yang; Jingjing Zhu ; Dr. Xiu-Jing Zheng; Prof. Guihua Tai; Prof. Xin-Shan Ye

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 356 KB
Volume: 17
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.201102615

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✦ Synopsis

Abstract

In this paper, a convenient approach to the synthesis of the repeating α‐(1→4)‐linked N‐acetyl galactosaminuronic acid units from the capsular polysaccharide of Salmonella typhi is reported. The exclusively α‐stereoselective glycosylation reactions were achieved by using oxazolidinone‐protected glycosides as building blocks based on a pre‐activation protocol. Di‐, tri‐, and tetrasaccharides were prepared by this short and efficient approach in high yields. The enzyme‐linked immunosorbent assay experiments show that our synthetic tri‐ and tetrasaccharide had much higher antigenic activities than previously reported ones in the inhibition of antibody binding by the native polysaccharide. The results demonstrate that the antigenic activities of saccharides can be strengthened greatly by increasing the number of acetyl groups present.

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