Enzyme-Catalyzed Synthesis of Aliphatic–Aromatic Oligoamides

• Published in: Biomacromolecules Vol. 14; no. 5; pp. 1600 - 1606
• Main Authors: Stavila, E, Alberda van Ekenstein, G. O. R, Loos, K
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 13-05-2013
• Subjects: Applied sciences; Biocatalysis; Carboxylic Ester Hydrolases - chemistry; Carboxylic Ester Hydrolases - isolation & purification; Decanoic Acids - chemistry; Diamines - chemistry; Enzymes, Immobilized - chemistry; Enzymes, Immobilized - isolation & purification; Exact sciences and technology; Fungal Proteins - chemistry; Fungal Proteins - isolation & purification; Fusarium - chemistry; Fusarium - enzymology; Hot Temperature; Isoenzymes - chemistry; Isoenzymes - isolation & purification; Nylons - chemical synthesis; Organic polymers; Phthalic Acids - chemistry; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts; Xylenes - chemistry; Catalytic reaction; Nylon; Solution polycondensation; Enzyme; Triacylglycerol lipase; Enzymatic catalysis; Esterases; Experimental study; Oligomer; Carboxylic ester hydrolases; Hydrolases; Catalyst activity; Immobilized enzyme
• ISSN: 1525-7797; 1526-4602
• DOI: 10.1021/bm400243a

Enzymatically catalyzed polycondensation of p-xylylenediamine and diethyl sebacate resulted in oligo(p-xylylene sebacamide) with high melting temperatures (223–230 °C) and the enzymatic polycondensation of dimethyl terephthalate and 1,8-diaminooctane leads to oligo(octamethylene terephthalamide) with two melting temperatures at 186 and 218 °C. No oligoamides, but products 1 and 2, were formed from the enzymatic reaction of dimethyl terephthalate and p-xylylenediamine. All reactions were catalyzed by CAL-B, icutinase, or CLEA cutinase. All reactions catalyzed by CAL-B show higher conversion than reactions catalyzed by icutinase or CLEA cutinase. The highest DPmax of 15 was achieved in a one-step and two-step synthesis of oligo(p-xylylene sebacamide) catalyzed by CLEA cutinase.