ArticleCommunications chemistry2024
Total synthesis of a structurally complex zwitterionic hexasaccharide repeating unit of polysaccharide B from Bacteroides fragilis via one-pot glycosylation.
Article in Communications chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Using Synthetic Glycans to Investigate Anti-Glycan Antibodies and Explore Their Medical Potential.Angewandte Chemie (International ed. in English) · 2026Review
- Chemical Synthesis and Immunological Evaluation of Escherichia coli O29, Shigella dysenteriae Serotype 11, and Proteus vulgaris O12 O-Antigen Oligosaccharides.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of Conjugation-Ready Sulfated Red Algae Carrageenan Oligosaccharides for Sensing Applications.Journal of the American Chemical Society · 2026Article
- Total synthesis of zwitterionic PS A2 oligosaccharides fromScience advances · 2025Article
- Total Synthesis and Anomeric Configuration Revision of Zwitterionic Polysaccharide A2's Pentasaccharide Repeating Unit fromJACS Au · 2025Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Zwitterionic polysaccharides (ZPSs) present on the surface of a common gut commensal Bacteroides fragilis are endowed with unique immunological properties as they can directly bind to T-cells in the absence of protein conjugation. ZPSs are therefore considered to be potential antigens for the development of totally carbohydrate-based vaccines. Herein, we disclose the first total synthesis of a highly branched phosphorylated zwitterionic capsular polysaccharide repeating unit of Bacteroides fragilis. The hexasaccharide repeating unit bearing six different monosaccharides comprises three 1,2-cis-glycosidic linkages, a challenging 1,2-trans linkage in D-QuipNAc-β-(1→4)-D-Gal motif, and a 2-aminoethyl phosphonate appendage. The synthesis of target ZPS was accomplished utilizing an expeditious, highly stereoselective and convergent (1 + 2 + 2 + 1) one-pot glycosylation strategy. The striking features include efficient synthesis of rare deoxy amino sugars D- and L-quinovosamine, stereoselective installation of three 1,2-cis glycosidic linkages, glycosylation of D-quinovosamine donor with a sterically crowded, poorly reactive 4-OH galactose moiety, as well as late stage phosphorylation.
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Registered trials
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