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

Qian Zhu, Zhengnan Shen, Fabrizio Chiodo, Simone Nicolardi, Antonio Molinaro, Alba Silipo () and Biao Yu ()
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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

Nature Communications, 2020, vol. 11, issue 1, 1-7

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-17992-x

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