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

Authors

  • Lin Yang,

    1. State Key Laboratory of Natural a0nd Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China)
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  • Jingjing Zhu ,

    1. State Key Laboratory of Natural a0nd Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China)
    2. School of Life Sciences, Northeast Normal University, Changchun 130024 (China)
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  • Dr. Xiu-Jing Zheng,

    1. State Key Laboratory of Natural a0nd Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China)
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  • Prof. Guihua Tai,

    1. School of Life Sciences, Northeast Normal University, Changchun 130024 (China)
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  • Prof. Xin-Shan Ye

    Corresponding author
    1. State Key Laboratory of Natural a0nd Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China)
    • State Key Laboratory of Natural a0nd Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191 (China)
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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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