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

✍ Scribed by R. Katsarava; V. Beridze; N. Arabuli; D. Kharadze; C. C. Chu; C. Y. Won

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 315 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990215)37:4<391::aid-pola3>3.0.co;2-e

✦ Synopsis

The purpose of this research was to synthesize new regular poly(ester amide)s (PEAs) consisting of nontoxic building blocks like hydrophobic ␣-amino acids, ␣,-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-(␣-amino acid) ␣,-alkylene diesters and di-p-nitrophenyl esters of diacids. Optimal conditions of this reaction have been studied. High molecular weight PEAs (M w ϭ 24,000-167,000) with narrow polydispersity (M w /M n ϭ 1.20-1.81) were prepared under the optimal reaction conditions and exhibited excellent filmforming properties. PEAs obtained are mostly amorphous materials with T g from 11 to 59°C. ␣-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.