Controlled synthesis of peptide-based amphiphilic copolymers

A synthetic route to the preparation of a lipophilic initiator and modified PEO-macroinitiators for ammonium-mediated polymerization of α-amino acid N-carboxy-anhydrides was presented. The multistep procedure involved the preparation of derivatives of maleic acid followed by a Michael addition of ammonium-containing thiols to the double bond. Amphiphilic hybrid block copolymers modified with dodecylamine or α-naphthylamine at the junction point were synthesized when the PEO-based macroinitiators were used. The presence of an optical lavel in the block copolymer containing naphthyl residue at the junction point enabled molar mass determination via UV analysis of copolymer solution in DMA. Experimental investigation concluded that the peptide-based amphiphiles have a potential application as surfactants or in encapsulation and delivery of drugs and other biological molecules.