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

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 un...

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Autores principales: Zhu, Qian, Shen, Zhengnan, Chiodo, Fabrizio, Nicolardi, Simone, Molinaro, Antonio, Silipo, Alba, Yu, Biao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7434892/
https://www.ncbi.nlm.nih.gov/pubmed/32811831
http://dx.doi.org/10.1038/s41467-020-17992-x
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author Zhu, Qian
Shen, Zhengnan
Chiodo, Fabrizio
Nicolardi, Simone
Molinaro, Antonio
Silipo, Alba
Yu, Biao
author_facet Zhu, Qian
Shen, Zhengnan
Chiodo, Fabrizio
Nicolardi, Simone
Molinaro, Antonio
Silipo, Alba
Yu, Biao
author_sort Zhu, Qian
collection PubMed
description 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.
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spelling pubmed-74348922020-08-28 Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus Zhu, Qian Shen, Zhengnan Chiodo, Fabrizio Nicolardi, Simone Molinaro, Antonio Silipo, Alba Yu, Biao Nat Commun Article 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. Nature Publishing Group UK 2020-08-18 /pmc/articles/PMC7434892/ /pubmed/32811831 http://dx.doi.org/10.1038/s41467-020-17992-x Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Zhu, Qian
Shen, Zhengnan
Chiodo, Fabrizio
Nicolardi, Simone
Molinaro, Antonio
Silipo, Alba
Yu, Biao
Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title_full Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title_fullStr Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title_full_unstemmed Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title_short Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus
title_sort chemical synthesis of glycans up to a 128-mer relevant to the o-antigen of bacteroides vulgatus
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7434892/
https://www.ncbi.nlm.nih.gov/pubmed/32811831
http://dx.doi.org/10.1038/s41467-020-17992-x
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