Amino acid-based bioanalogous polymers. Synthesis, and study of regular poly(ester amide)s based on bis(?-amino acid) ?,?-alkylene diesters, and aliphatic dicarboxylic acids

Abstract

The purpose of this research was to synthesize new regular poly(ester amide)s (PEAs) consisting of nontoxic building blocks like hydrophobic α-amino acids, α,ω-diols, and aliphatic dicarboxylic acids, and to examine the effects of the structure of these building block components on some physico-chemical and biochemical properties of the polymers. PEAs were prepared by solution polycondensation of di-p-toluenesulfonic acid salts of bis-(α-amino acid) α,ω-alkylene diesters and di-p-nitrophenyl esters of diacids. Optimal conditions of this reaction have been studied. High molecular weight PEAs (Mw = 24,000–167,000) with narrow polydispersity (Mw/Mn = 1.20–1.81) were prepared under the optimal reaction conditions and exhibited excellent film-forming properties. PEAs obtained are mostly amorphous materials with Tg from 11 to 59°C. α-Chymotrypsin catalyzed in vitro hydrolysis of these new PEA substrates was studied to assess the effect of the building blocks of these new polymers on their biodegradation properties. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 391–407, 1999