Enzymatic resolution of ibuprofen in an organic solvent under ultrasound irradiation.
Ultrasound has been successfully adopted to improve the biocatalytic properties of APE1547 (a novel esterase from the archaeon Aeropyrum pernix K1) in the resolution of ibuprofen. After optimizing the conditions (ultrasound power, 200 W; temperature, 35 °C), the best biocatalytic performance of APE1547 (enzyme activity, 5.39 µmol/H/mg; E value, 130.8) was obtained. Compared with the conventional reaction in an orbital shaker, the enzyme activity was significantly enhanced about 90-fold, and the enantioselectivity was enhanced about fourfold after an ultrasound. The results of scanning electron microscopy clearly indicated that the activation effect of ultrasound on APE1547 originated mainly in the morphological change of the enzyme powder. Both lower particle size and conformational change of APE1547 under ultrasound might be helpful to enhance the enantioselectivity. In addition, APE1547 kept its best performance under the low-power ultrasound for at least five reaction cycles.
Liaoning Key Laboratory of Urban Integrated Pest Management and Ecological Security, Shenyang University, Shenyang, People's Republic of China; Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun, People's Republic of China.
Dantong
D
Zhao
Hong
H
Yue
Ge
G
Chen
Liyan
L
Jiang
Hong
H
Zhang
Zhi
Z
Wang
Guangchun
G
Liu
D041522:Aeropyrum / Q000201:enzymology*; D055162:Biocatalysis; D004950:Esterases / Q000737:chemistry*; D007052:Ibuprofen / Q000737:chemistry / Q000378:metabolism* / Q000528:radiation effects; D009930:Organic Chemicals / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D014465:Ultrasonics
D009930:Organic Chemicals; D012997:Solvents; D004950:Esterases; D007052:Ibuprofen
APE1547; enantioselectivity; enzyme activity; esterification; ibuprofen; ultrasound