Preparation of synthetic glycoconjugates as potential vaccines against Shigella flexneri serotype 2a disease

Abstract

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-deoxy-β-D-glucopyranoside acceptor. Use of thiol–maleimide coupling chemistry allowed site-selective efficient conjugation.