Two Enzyme Cooperatively Catalyzed Tandem Polymerization for the Synthesis of Polyester Containing Chiral ( R)‐ or ( S)‐Ibuprofen Pendants

• Published in: Macromolecular Rapid Communications
• Main Authors: Qian, Xueqi, Wang, Jianfeng, Li, Yanyan, Lin, Xianfu, Wu, Qi
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2014
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/marc.201400394; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fmarc.201400394; https://onlinelibrary.wiley.com/doi/pdf/10.1002/marc.201400394

An interesting cooperation between Candida antarctica Lipase B (CAL‐B) and alkaline protease from Bacillus subtilis (BSP) in the copolymerization of bulky ibuprofen‐containing hydroxyacid methyl ester (HAEP) and ε ‐caprolactone ( ε ‐CL) is observed. This cooperation improved the of the polymers from 3130 (CAL‐B) to 9200 g mol –1 (CAL‐B/BSP). Experimental results clearly indicate that CAL‐B mainly catalyzes the ring‐opening polymerization (ROP) of ε ‐CL under the initiation of HAEP to form the homopolymer of ε ‐CL, while BSP catalyzes the subsequent polycondensation of the ROP product to yield the copolymer with increased molecular weight. Furthermore, using suitable chemo‐enzymatic methods, valuable polyesters with chiral ( R )‐ or ( S )‐ibuprofen pendants can be tailor‐made. image