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Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus

Author

Listed:
  • Qian Zhu

    (State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Zhengnan Shen

    (School of Physical Science and Technology, ShanghaiTech University)

  • Fabrizio Chiodo

    (Department of Molecular Cell Biology and Immunology, Amsterdam Infection and Immunity Institute, De Boelelaan 1108)

  • Simone Nicolardi

    (Center for Proteomics and Metabolomics, Leiden University Medical Center)

  • Antonio Molinaro

    (Department of Chemical Sciences, University of Naples Federico II)

  • Alba Silipo

    (Department of Chemical Sciences, University of Naples Federico II)

  • Biao Yu

    (State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences
    School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-Lane Xiangshan)

Abstract

Glycans are involved in various life processes and represent critical targets of biomedical developments. Nevertheless, the accessibility to long glycans with precise structures remains challenging. Here we report on the synthesis of glycans consisting of [→4)-α-Rha-(1 → 3)-β-Man-(1 → ] repeating unit, which are relevant to the O-antigen of Bacteroides vulgatus, a common component of gut microbiota. The optimal combination of assembly strategy, protecting group arrangement, and glycosylation reaction has enabled us to synthesize up to a 128-mer glycan. The synthetic glycans are accurately characterized by advanced NMR and MS approaches, the 3D structures are defined, and their potent binding activity with human DC-SIGN, a receptor associated with the gut lymphoid tissue, is disclosed.

Suggested Citation

  • Qian Zhu & Zhengnan Shen & Fabrizio Chiodo & Simone Nicolardi & Antonio Molinaro & Alba Silipo & Biao Yu, 2020. "Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus," Nature Communications, Nature, vol. 11(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-17992-x
    DOI: 10.1038/s41467-020-17992-x
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    Cited by:

    1. Jing Zhang & Zhao-Xiang Luo & Xia Wu & Chen-Fei Gao & Peng-Yu Wang & Jin-Ze Chai & Miao Liu & Xin-Shan Ye & De-Cai Xiong, 2023. "Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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