Skip to Main content Skip to Navigation
Journal articles

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.
Complete list of metadatas

https://hal-pasteur.archives-ouvertes.fr/pasteur-02043358
Contributor : Laurence Mulard <>
Submitted on : Wednesday, February 20, 2019 - 11:22:11 PM
Last modification on : Friday, March 27, 2020 - 2:38:00 AM

Identifiers

Collections

Citation

Hélène Pfister, Laurence Mulard. Synthesis of the Zwitterionic Repeating Unit of the O-Antigen from Shigella sonnei and Chain Elongation at Both Ends. Organic Letters, American Chemical Society, 2014, 16 (18), pp.4892-4895. ⟨10.1021/ol502395k⟩. ⟨pasteur-02043358⟩

Share

Metrics

Record views

141