Premium
Amino acid based bioanalogous polymers. Synthesis of novel poly(urethane amide)s based on N,N ′‐(trimethylenedioxydicarbonyl)bis(phenylalanine)
Author(s) -
Kartvelishvili Tamara,
Kvintradze Akaki,
Katsarava Ramaz
Publication year - 1996
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1996.021970119
Subject(s) - dipeptide , phenylalanine , condensation polymer , tripeptide , chemistry , amide , amino acid , moiety , polymer chemistry , trimethylsilyl , polymer , hexamethylenediamine , peptide synthesis , organic chemistry , polyamide , biochemistry
The feasibility of synthesizing high‐molecular‐weight amino acid based bioanalogous polymers (AABBPs)‐poly(urethane amide)s (PUA) — via polycondensation (PC) of di‐ p ‐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 (η red = 1,53 dL/g) was obtained by PC of 3 with hexamethylenediamine. A dipeptide (Phe‐Phe) containing regular poly(ester urethane amide) (η 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 (η 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).