Improvements of enzyme activity and enantioselectivity via combined substrate engineering and covalent immobilization

Biotechnology and Bioengineering
Pei-Yun WangTeh-Liang Chen

Abstract

Esterases, lipases, and serine proteases have been applied as versatile biocatalysts for preparing a variety of chiral compounds in industry via the kinetic resolution of their racemates. In order to meet this requirement, three approaches of enzyme engineering, medium engineering, and substrate engineering are exploited to improve the enzyme activity and enantioselectivity. With the hydrolysis of (R,S)-mandelates in biphasic media consisting of isooctane and pH 6 buffer at 55 degrees C as the model system, the strategy of combined substrate engineering and covalent immobilization leads to an increase of enzyme activity and enantioselectivity from V(S)/(E(t)) = 1.62 mmol/h g and V(S)/V(R) = 43.6 of (R,S)-ethyl mandelate (1) for a Klebsiella oxytoca esterase (named as SNSM-87 from the producer) to 16.7 mmol/h g and 867 of (R,S)-2-methoxyethyl mandelate (4) for the enzyme immobilized on Eupergit C 250L. The analysis is then extended to other (R,S)-2-hydroxycarboxylic acid esters, giving improvements of the enzyme performance from V(S)/(E(t)) = 1.56 mmol/h g and V(S)/V(R) = 41.9 of (R,S)-ethyl 3-chloromandelate (9) for the free esterase to 39.4 mmol/h g and 401 of (R,S)-2-methoxyethyl 3-chloromandelate (16) for the immobilized enz...Continue Reading

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Citations

Jul 11, 2009·Biotechnology Letters·Dean Brady, Justin Jordaan
Oct 12, 2012·Applied Biochemistry and Biotechnology·Jiao-Jiao ShangguanJian-He Xu
Aug 12, 2014·Applied Microbiology and Biotechnology·Jiali GuHongwei Yu
Apr 14, 2009·Bioresource Technology·Jong Ho LeeSeung Wook Kim
Jan 12, 2013·International Journal of Molecular Sciences·Raushan Kumar SinghJung-Kul Lee
Feb 1, 2019·Bioscience Reports·Clare F Megarity
Oct 8, 2009·Bioscience, Biotechnology, and Biochemistry·Ye-Wang ZhangJung-Kul Lee
Oct 28, 2019·International Journal of Molecular Sciences·Luuk MestromPeter-Leon Hagedoorn
May 31, 2019·Applied Biochemistry and Biotechnology·Alberto Del Monte-MartínezJosé M Guisán

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