Amino acid based bioanalogous polymers. Synthesis of novel poly(urethane amide)s based on N,N'-(trimethylenedioxydicarbonyl)bis(phenylalanine)

The feasibility of synthesizing high-molecular-weight amino acid based bioanalogous polymers (AABBPs)-poly(urethane amide)s (PUA) - via polycondensation (PC) of dip-nitrophenyl ester of N,N'-(trimethylenedioxydicarbonyl)bis(L-phenylalanine) (3) with diamines or their derivatives under mild conditions in organic solvents was studied for the first time. A regular PUA (eta(red) = 1,53 dL/g) was obtained by PC of 3 with hexamethylenediamine. A dipeptide (Phe-Phe) containing regular poly(ester urethane amide) (eta(red) = 0,58 dL/g) was synthesized by PC of 3 with p-toluenesulfonic acid salt of bis(L-phenylalanine) 1,4-butylene diester. A tripeptide (Phe-Lys-Phe) containing PUA (eta(red) = 0,38 dL/g) with pendent ester groups was prepared via PC of 3 with N,N-bis(trimethylsilyl)-L-lysine methyl ester. These novel AABBPs which may be considered as structural analogs of AB type bioanalogous polymers - conventional poly(amino acids) are of interest in enzymology, immunology, pharmacology, and biotechnology (as materials for biomedical applications).