Journal of the Chinese Chemical Society p. 696 - 705 (2018)
Update date:2022-08-28
Topics:
Gu, Yaohua
Xue, Ping
Magnetic porous polymeric microspheres containing epoxy groups were prepared by suspension polymerization (denoted as magnetic Fe3O4@GEM microspheres). Fe3O4@GEM with a specific surface area of 30.41 m2/g, average pore diameter of 17.13 nm, and pore volume of 0.13 cm3/g exhibited superparamagnetic behavior with the saturation magnetization of 7.1 emu/g. The content of epoxy groups on Fe3O4@GEM was 0.22 mmol/g. Pseudomonas sp. lipase (PSL) was covalently immobilized onto the Fe3O4@GEM microspheres through the reaction between the amino groups of the enzyme and the epoxy groups on the microspheres. PSL/Fe3O4@GEM exhibited enhanced enantioselectivity for the resolution of allylic alcohol to the corresponding optically active (S)-allylic alcohol and (R)-allylic alcohol acetate compared to free PSL. The enantiomeric excess of (S)-l-pheny-2-propen-1-ol for the former (98.1%) was 81.7 times that of the latter (1.2%) when the immobilized PSL was used for transesterification resolution of (R,S)-l-pheny-2-propen-1-ol. Furthermore, the ees and eep values were still retained at 95.2% and 95.4% after PSL/Fe3O4@GEM was recycled 10 times, indicating that PSL/Fe3O4@GEM had very good reusability. In addition, the transesterification resolution of (R,S)-1-(4-methylphenyl)-2-propen-1-ol and (R,S)-1-(4-bromophenyl)-2-propen-1-ol was catalyzed by PSL/Fe3O4@GEM, affording ideal ees and eep values of 99.3%, 97.4% and 99.6%, 98.2%, respectively. Therefore, PSL/Fe3O4@GEM demonstrated its potential as a highly efficient enzymatic reactor and Fe3O4@GEM would be very promising carriers for immobilizing enzymes in industrial application.
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