Preparation of synthetic glycoconjugates as potential vaccines against Shigella flexneri serotype 2a disease.
The synthesis of three neoglycopeptides incorporating carbohydrate haptens, differing in length, covalently linked to a non natural universal T helper peptide is disclosed. They were synthesized according to a blockwise strategy based on the condensation of appropriate di-, tri-, and tetrasaccharide trichloroacetimidate donors onto an azidoethyl 2-acetamido-2-deoxybeta-D-glucopyranoside acceptor. Use of thiol-maleimide coupling chemistry allowed site-selective efficient conjugation.
Wright
Karen
K
Unité de Chimie Organique, URA CNRS 2128, Institut Pasteur, 28 rue du Dr Roux, 75 724, Paris15, France.
Guerreiro
Catherine
C
Laurent
Isabelle
I
Baleux
Françoise
F
Mulard
Laurence A
LA
D000117:Acetylglucosamine / Q000737:chemistry; D000942:Antigens, Bacterial / Q000737:chemistry; D002236:Carbohydrate Conformation; D018985:Epitopes, B-Lymphocyte / Q000737:chemistry; D018984:Epitopes, T-Lymphocyte / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000276:immunology; D006020:Glycopeptides / Q000138:chemical synthesis; D006031:Glycosylation; D008070:Lipopolysaccharides / Q000737:chemistry; D008239:Lysine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D017780:Malaria Vaccines / Q000737:chemistry*; D015394:Molecular Structure; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis; D025942:Oligosaccharides, Branched-Chain / Q000138:chemical synthesis; D012210:Rhamnose / Q000737:chemistry; D012763:Shigella flexneri / Q000276:immunology*; D018074:Vaccines, Conjugate / Q000737:chemistry* / Q000276:immunology; D014614:Vaccines, Synthetic / Q000737:chemistry
D000942:Antigens, Bacterial; D018985:Epitopes, B-Lymphocyte; D018984:Epitopes, T-Lymphocyte; D006001:Glycoconjugates; D006020:Glycopeptides; D008070:Lipopolysaccharides; D017780:Malaria Vaccines; D019081:O Antigens; D009844:Oligosaccharides; D025942:Oligosaccharides, Branched-Chain; C401223:PADRE 45; D018074:Vaccines, Conjugate; D014614:Vaccines, Synthetic; D005947:Glucose; D008239:Lysine; D012210:Rhamnose; D000117:Acetylglucosamine