Related Experiment Video
Updated: Nov 9, 2025

The Application of Open Searching-based Approaches for the Identification of Acinetobacter baumannii O-linked Glycopeptides
Published on: November 2, 2021
Total Synthesis of the Repeating Unit of Bacteroides fragilis Zwitterionic Polysaccharide A1
Ennus K Pathan1, Bhaswati Ghosh1, Ananda Rao Podilapu1
1Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
Abstract:
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 S2 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.
More Related Videos
Related Concept Videos
Peptidoglycan Synthesis
Formation of Lipopolysaccharides
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Proteoglycans
Biosynthesis of Polysaccharides
Bacterial Phylum Bacteroidota

