Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
| Autor: | Biao Yu, Simone Nicolardi, Zhengnan Shen, Qian Zhu, Antonio Molinaro, Alba Silipo, Fabrizio Chiodo |
|---|---|
| Přispěvatelé: | Zhu, Q., Shen, Z., Chiodo, F., Nicolardi, S., Molinaro, A., Silipo, A., Yu, B., Molecular cell biology and Immunology |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Lipopolysaccharides
0301 basic medicine Glycan Magnetic Resonance Spectroscopy Glycosylation Science Carbohydrates Glycobiology General Physics and Astronomy Lipopolysaccharide 02 engineering and technology Chemical synthesis Article General Biochemistry Genetics and Molecular Biology 03 medical and health sciences chemistry.chemical_compound Antigen Polysaccharides Bacteroides vulgatus Bacteroides Humans lcsh:Science Polysaccharide Protecting group chemistry.chemical_classification O Antigen Multidisciplinary biology Chemistry O Antigens General Chemistry Oligosaccharide 021001 nanoscience & nanotechnology Gastrointestinal Microbiome carbohydrates (lipids) Bacteroide 030104 developmental biology Biochemistry Spectrometry Mass Matrix-Assisted Laser Desorption-Ionization biology.protein lcsh:Q Natural product synthesis 0210 nano-technology Human |
| Zdroj: | Nature Communications Nature Communications, 11(1). NATURE RESEARCH Chiodo, F 2020, ' Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus ', Nature Communications, vol. 11, no. 1, 4142 . https://doi.org/10.1038/s41467-020-17992-x Nature Communications, Vol 11, Iss 1, Pp 1-7 (2020) Nature Communications, 11(1):4142. Nature Publishing Group |
| ISSN: | 2041-1723 |
| Popis: | 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. Glycans are abundant biomolecules that mediate essential biological processes, but their chemical synthesis is challenging. Here, the authors report the synthesis of glycans up to a 128-mer, which represents the O-antigen of Bacteroides vulgatus lipopolysaccharide and one of the longest synthetic glycans to date. |
| Databáze: | OpenAIRE |
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