Synthesis of the Zwitterionic Repeating Unit of the O-Antigen from Shigella sonnei and Chain Elongation at Both Ends

Abstract : Shigella sonnei O-antigen features a zwitterionic disaccharide repeat encompassing two rare monosaccharides. The synthesis of the AB repeat and of trisaccharides ABA' and B'AB, which validates chain elongation at either end, is reported. All targets were synthesized using a postglycosylation oxidation strategy in combination with imidate chemistry. Precursors to residue A were obtained from L-glucose. The AAT (B) donor and acceptor were obtained from D-glucosamine. A one-step Pd(OH)2/C-mediated deprotection provided the propyl glycoside targets.