Total synthesis of zwitterionic PS A2 oligosaccharides from <i>Bacteroides fragilis</i>.
basic_science · Level V
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- Record sourced from PubMed, PMID 41385639.
- Also identified by DOI 10.1126/sciadv.aeb4065 and PMC identifier 12700203.
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Abstract
Zwitterionic polysaccharides have unique structures and can elicit T cell-dependent immune responses. To unravel their molecular mode of action and develop potential alternatives for carrier proteins in carbohydrate-based vaccines, we here describe a total synthesis of zwitterionic PS A2 oligosaccharides from <i>Bacteroides fragilis</i>. The pentasaccharide and decasaccharide bearing one or two repeating units were efficiently synthesized via convergent glycosylation strategy. The ingenious protecting groups have enabled the stereoselectivity of glycosylation. A unique synthetic approach was developed to introduce the chiral 3-hydroxybutanoic acid side chain on mannoheptose, which proved very challenging to form in this skeleton.
Medical subject headings
- Bacteroides fragilis
- Oligosaccharides
- Polysaccharides, Bacterial