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Pseudomonas sp. Lipase Immobilized on Magnetic Porous Polymer Microspheres as an Effective and Recyclable Biocatalyst for Resolution of Allylic Alcohols
Author(s) -
Gu Yaohua,
Xue Ping
Publication year - 2018
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201700424
Subject(s) - chemistry , allylic rearrangement , transesterification , nuclear chemistry , lipase , vinyl alcohol , immobilized enzyme , biocatalysis , polymer chemistry , catalysis , organic chemistry , polymer , ionic liquid , enzyme
Magnetic porous polymeric microspheres containing epoxy groups were prepared by suspension polymerization (denoted as magnetic Fe 3 O 4 @GEM microspheres). Fe 3 O 4 @GEM with a specific surface area of 30.41 m 2 /g, average pore diameter of 17.13 nm, and pore volume of 0.13 cm 3 /g exhibited superparamagnetic behavior with the saturation magnetization of 7.1 emu/g. The content of epoxy groups on Fe 3 O 4 @GEM was 0.22 mmol/g. Pseudomonas sp. lipase (PSL) was covalently immobilized onto the Fe 3 O 4 @GEM microspheres through the reaction between the amino groups of the enzyme and the epoxy groups on the microspheres. PSL/Fe 3 O 4 @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 ee s and ee p values were still retained at 95.2% and 95.4% after PSL/Fe 3 O 4 @GEM was recycled 10 times, indicating that PSL/Fe 3 O 4 @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/Fe 3 O 4 @GEM, affording ideal ee s and ee p values of 99.3%, 97.4% and 99.6%, 98.2%, respectively. Therefore, PSL/Fe 3 O 4 @GEM demonstrated its potential as a highly efficient enzymatic reactor and Fe 3 O 4 @GEM would be very promising carriers for immobilizing enzymes in industrial application.