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Tailoring magnetic mesoporous silica spheres-immobilized lipase for kinetic resolution of methyl 2-bromopropionate in a co-solvent system

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Abstract

We report the facile synthesis of magnetic mesoporous silica spheres (MMSS) by combining the hydrothermal method and pyrolysis process. The mesostructure, morphology and magnetization of the as-synthesized MMSS can be tailored by adjusting the mass ratio of trimethyl benzene-to-Pluronic P123 triblock copolymer (EO20PO70EO20, MW = 5800; P123) and the amount of ferric acetylacetonate. Lipase from Candida cylindracea (CCL) immobilized by the resulting MMSS with well-defined microsphere structure, uniform mesopore size (~ 6.7 nm), large surface area (515 m2 g−1) and high saturated magnetization (8.7 emu g−1) was employed for kinetic resolution of methyl 2-bromopropionate in aqueous buffer/organic co-solvent; as a result, excellent catalytic performance was obtained with 18% chemical yield and 96.2% enantiomeric excess (eeS) of methyl (S)-2-bromopropionate. Moreover, the CCL/MMSS can be easily separated from the reaction system for repetition due to high magnetization, and exhibits a superior stability (83.2% retention) even after 8 cycles in terms of yield and eeS.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21263020), the project of Key Laboratory of Powder Materials and Special Ceramics (1408) and the Research Project of Ningxia Colleges and Universities (NGY2015160).

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Authors and Affiliations

  1. School of Materials Science and Engineering, North Minzu University, Yinchuan, 750021, China

    Xiang-Hui Yan

  2. Key Laboratory of Energy Resources and Chemical Engineering, Ningxia University, Yinchuan, 750021, China

    Ping Xue

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  1. Xiang-Hui Yan
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  2. Ping Xue
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Correspondence to Xiang-Hui Yan or Ping Xue.

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Yan, XH., Xue, P. Tailoring magnetic mesoporous silica spheres-immobilized lipase for kinetic resolution of methyl 2-bromopropionate in a co-solvent system. Res Chem Intermed 44, 4295–4306 (2018). https://doi.org/10.1007/s11164-018-3369-1

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