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1. (Article ID: 6123)
Pathan EK, Ghosh B, Podilapu AR, Kulkarni SS
Total Synthesis of the Repeating Unit of Bacteroides fragilis Zwitterionic Polysaccharide A1
Journal of Organic Chemistry 86(9) (2021)
6090-6099
Zwitterionic polysaccharides isolated from commensal bacteria are endowed with unique immunological properties and are emerging as immunotherapeutic agents as well as vaccine carriers. Reported herein is a total synthesis of the repeating unit of Bacteroides fragilis zwitterionic polysaccharide A1 (PS A1). The structurally complex tetrasaccharide unit contains a rare sugar 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT) and two consecutive 1,2-cis glycosidic linkages. The repeating unit was efficiently assembled by rapid synthesis of d-galactosamine and AAT building blocks from cheap and abundant d-mannose via a one-pot SN2 displacement of 2,4-bistriflates and installation of all of the glycosidic bonds in a highly stereoselective manner. The total synthesis involves a longest linear sequence of 17 steps with 3.47% overall yield.
synthesis, repeating unit, vaccine, Bacteroides fragilis, total synthesis, zwitterionic polysaccharide A1
NCBI PubMed ID: 33843231Publication DOI: 10.1021/acs.joc.0c02935Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: Suvarn S. Kulkarni <: suvarn
chem.iitb.ac.in>
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, HPLC, glycosylation, optical rotation measurement, HR-ESI-MS
The publication contains the following compound(s):
- Compound ID: 403
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R-Pyr-(2-6:2-4)-+
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b-D-Galf-(1-3)-+ |
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-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: zwitterionic polysaccharide A1, zwitterionic polysaccharide, PS A1, polysaccharide A1
Compound class: CPS
- Compound ID: 15821
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R-Pyr-(2-6:2-4)-+
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b-D-Galf-(1-3)-+ |
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a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-Galp-(1-1)-Pr |
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Structure type: oligomer
Trivial name: zwitterionic polysaccharide A1
Compound class: CPS
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