Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 32811831.
- Also identified by DOI 10.1038/s41467-020-17992-x and PMC identifier 7434892.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
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.
Medical subject headings
- Bacteroides
- O Antigens
- Polysaccharides