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-deoxyβ-D-glucopyranoside acceptor. Use of thiol-maleimide coupling chemistry allowed site-selective efficient conjugation.
conformation, Shigella flexneri, epitopes, glycoconjugates, glycosylation, vaccine, chemical synthesis, T-Lymphocyte, glycopeptides
NCBI PubMed ID: 15136809Journal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: lmulard@pasteur.fr
Institutions: Unite de Chimie Organique, URA CNRS 2128, Institut Pasteur, 28 rue du Dr Roux, 75 724, Paris15, France
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, MALDI-MS, CI-MS
Found