Efficient transesterification 4-hydroxytetrahydropyran immobilized lipase resolution of 2-（4-chlorophenyl）- with magnetically separable

We report an efficient kinetic resolution of racemic 2-（4-chlorophenyl）-4-hydroxytetrahydro-pyran （CLP-4-HTHP） via Pseudomonas cepacia lipase （PSL）-catalyzed transesterification, where PSL is immobilized on a core-shell MnFe204@SiO2-（CH2）3-NH2 carrier and used as a magnetically separable catalyst. T...

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Published in中国化学快报：英文版 no. 12; pp. 1112 - 1114
Main Author Ping Xue Zhen-Zhen Kang Xiao-Yong Lai Guan-Qun Qu Yuan-Yuan Li
Format Journal Article
LanguageEnglish
Published 2013
Subjects
四氢吡喃
固定化
氯苯基
磁分离
羟基
脂肪酶
酯交换反应
酶分解
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Summary:We report an efficient kinetic resolution of racemic 2-（4-chlorophenyl）-4-hydroxytetrahydro-pyran （CLP-4-HTHP） via Pseudomonas cepacia lipase （PSL）-catalyzed transesterification, where PSL is immobilized on a core-shell MnFe204@SiO2-（CH2）3-NH2 carrier and used as a magnetically separable catalyst. The as-synthesized PSL/MnFe204@SiO2-（CH2）3-NH2 catalyst exhibits enhanced catalytic activity for resolving racemic CLP-4-HTHP to the corresponding optically pure （2R,4S）-CLP-4-HTHP compared to the free PSL. The ees for the former is 2.3 times larger than that for the latter under optimized conditions （99.4% and 44.1%, respectively）, although the eep for them are same （99.2%）. Meanwhile, the PSL/MnFe204@SiO2-（CH2）3-NH2 catalyst possesses a high saturate magnetization of 59.7 emu/g and could be easily recovered by magnetic separation and reused. The catalytic activity in six recycling tests did not significantly decrease, suggesting its great potential for industrial applications.
Bibliography:11-2710/O6
We report an efficient kinetic resolution of racemic 2-（4-chlorophenyl）-4-hydroxytetrahydro-pyran （CLP-4-HTHP） via Pseudomonas cepacia lipase （PSL）-catalyzed transesterification, where PSL is immobilized on a core-shell MnFe204@SiO2-（CH2）3-NH2 carrier and used as a magnetically separable catalyst. The as-synthesized PSL/MnFe204@SiO2-（CH2）3-NH2 catalyst exhibits enhanced catalytic activity for resolving racemic CLP-4-HTHP to the corresponding optically pure （2R,4S）-CLP-4-HTHP compared to the free PSL. The ees for the former is 2.3 times larger than that for the latter under optimized conditions （99.4% and 44.1%, respectively）, although the eep for them are same （99.2%）. Meanwhile, the PSL/MnFe204@SiO2-（CH2）3-NH2 catalyst possesses a high saturate magnetization of 59.7 emu/g and could be easily recovered by magnetic separation and reused. The catalytic activity in six recycling tests did not significantly decrease, suggesting its great potential for industrial applications.
Optically pure 2-（4-chlorophenyl）-4- hydroxytetrahydropyran Magnetically immobilized lipase Enanatioselectivity Asymmetric transesterification
ISSN:1001-8417
1878-5964