Synthesis of structurally-controlled AIDS vaccine model with glyco-peptide dendrimer scaffolds

A novel glyco-peptide dendrimer-type AIDS vaccine model with a well-defined structure was synthesized. A low-substituted, monodispersed, glyco-peptide dendrimer was prepared by binding maltose to a proline-poly(lysine) dendrimer with monofunctional prolyl amino groups on the periphery. To the hemispherical maltose-proline-poly(lysine) dendrimer, succinic anhydride was reacted to provide succinylated dendrimer with an average of 13 succinyl carboxyl groups per dendrimer. The reactivity of succinyl-maltose-proline-poly(lysine) dendrimer was investigated by coupling a tripeptide to the carboxyl group in water using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) as a condensing agent. By binding two kinds of peptide sequences included in the envelope glycoprotein of HIV to the dendrimer, AIDS vaccine models with glyco-peptide dendrimer scaffold were synthesized. The structure of the vaccine models was determined by NMR and MALDI-TOF mass analyses.