Carbohydrates populate the cell surfaces of countless viruses, parasites, and bacteria. Due to the prevalence of these biomolecules, glycan-protein molecular recognition processes are crucial in understanding the immune response to pathogens. Here, we report the synthesis of the phosphoethanolamine (PEtN) modified zwitterionic polysaccharide repeating unit of Photorhabdus temperata ssp. cinereal 3240. To this end, the 32-step synthesis involves the stereo- and regioselective assembly of the repeating unit with a deoxyamino sugar AAT at the non-reducing end, two consecutive 1,2-trans glycosidic linkages and H-phosphonate chemistry to install the PEtN arm on a sterically hindered and poorly reaction C-4 alcohol.

Synthesis and biological investigation of zwitterionic polysaccharides

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.