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Enantioselective Resolution of (R, S)-2-Phenoxy-Propionic Acid Methyl Ester by Covalent Immobilized Lipase from Aspergillus oryzae

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Abstract

(R)-2-Phenoxy-propionic acid methyl ester (PPAM) is an important chiral precursor of aryloxy phenoxy propionate herbicides. The covalent immobilization of lipase from Aspergillus oryzae WZ007 and the catalysis of enantioselective (R, S)-PPAM resolution by the immobilized A. oryzae lipase (AOL) were investigated in this study. The primary amino resin LX-1000HA was selected as the support for the covalent immobilization of AOL. The Km and Vmax of the immobilized lipase were 1.97 mM and 4.84 × 103 μmol/mg min, respectively. The key reaction parameters (pH, temperature, rotation speed, and substrate concentration) for the lipase-catalyzed resolution of (R, S)-PPAM were optimized. An e.e.s of 99.5% and conversion rate of 50.8% were achieved under the optimal conditions of pH 7.5, 30 °C, and substrate concentration 500 mM. The immobilized lipase retained 87.3% of its initial activity after 15 cycles of the repeated experiments. The results demonstrated that the covalent immobilized AOL has potential industrial applications.

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Acknowledgments

This research was financially supported by the National Natural Science Foundation of China (no. 31600639, no. 31660247) and the Education Department of Jiangxi Province (GJJ151211).

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Authors and Affiliations

  1. Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, Zhejiang, People’s Republic of China

    Weichao Zhong, Mengjie Zhang, Yinjun Zhang, Zhao Wang & Jianyong Zheng

  2. School of Medicine and Life Sciences, Xinyu University, Xinyu, Jiangxi, People’s Republic of China

    Xiaojun Li

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  1. Weichao Zhong
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  2. Mengjie Zhang
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  3. Xiaojun Li
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  4. Yinjun Zhang
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  5. Zhao Wang
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Correspondence to Jianyong Zheng.

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E-supplementary data of this work can be found in online version of the paper, at https://doi.org/10.1016/.2019.00.000.

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Zhong, W., Zhang, M., Li, X. et al. Enantioselective Resolution of (R, S)-2-Phenoxy-Propionic Acid Methyl Ester by Covalent Immobilized Lipase from Aspergillus oryzae. Appl Biochem Biotechnol 190, 1049–1059 (2020). https://doi.org/10.1007/s12010-019-03145-4

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  • DOI: https://doi.org/10.1007/s12010-019-03145-4

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