title: 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.
authors.affiliation: Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724 Paris Cedex 15, France.
authors.forename: Hélène B
authors.initials: HB
authors.lastname: Pfister
authors.forename: Laurence A
authors.initials: LA
authors.lastname: Mulard
mesh_terms: D004187:Disaccharides / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D019081:O Antigens / Q000737:chemistry*; D012764:Shigella sonnei / Q000276:immunology*; D014312:Trisaccharides / Q000737:chemistry
chemical_list: D004187:Disaccharides; D009005:Monosaccharides; D019081:O Antigens; D014312:Trisaccharides; D005947:Glucose