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Asymmetric Hydrogenation of C = C Bonds in a SpinChem Reactor by Immobilized Old Yellow Enzyme and Glucose Dehydrogenase

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Abstract

The application of immobilized enzymes in pharmaceutical and bulk chemical production has been shown to be economically viable. We demonstrate the exceptional performance of a method that immobilizes the old yellow enzyme YqjM and glucose dehydrogenase (GDH) on resin for the asymmetric hydrogenation (AH) of C = C bonds in a SpinChem reactor. When immobilized YqjM and GDH are reused 10 times, the conversion of 2-methylcyclopentenone could reach 78%. Which is because the rotor of the SpinChem reactor effectively reduces catalyst damage caused by shear force in the reaction system. When the substrate concentration is 175 mM, an 87% conversion of 2-methylcyclopentenone is obtained. The method is also observed to perform well for the AH of C = C bonds in other unsaturated carbonyl compounds with the SpinChem reactor. Thus, this method has great potential for application in the enzymatic production of chiral compounds.

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Acknowledgements

Thanks to Professor Frank Hollamann of the Delft University of Technology for selflessly providing the plasmid of YqjM.

Funding

This work was supported by the National Nature Science Foundation of China (Nos. 22078081, 21878068, and 21901058) and the Natural Science Foundation of Hebei Province (B2019202216).

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin, 300130, People’s Republic of China

    Teng Ma, Weixi Kong, Yunting Liu, Hao Zhao, Yaping Ouyang, Jing Gao, Liya Zhou & Yanjun Jiang

  2. Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin, 300130, People’s Republic of China

    Teng Ma, Weixi Kong, Yunting Liu, Hao Zhao, Yaping Ouyang, Jing Gao, Liya Zhou & Yanjun Jiang

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  1. Teng Ma
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Contributions

Teng Ma: Methodology, validation, formal analysis, visualization, writing (original draft), writing (review and editing).

Weixi Kong: Methodology, validation, formal analysis.

Yunting Liu: Conceptualization, formal analysis, investigation, writing (review and editing), supervision.

Hao Zhao: Writing (review and editing), supervision.

Yaping Ouyang: Validation, formal analysis.

Jing Gao: Writing (review and editing), supervision.

Liya Zhou: Writing (review and editing), supervision.

YanJun Jiang: Conceptualization, investigation, writing (review and editing), supervision.

Corresponding authors

Correspondence to Liya Zhou or Yanjun Jiang.

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This is an observational study. The Hebei University of Technology Research Ethics Committee has confirmed that no ethical approval is required.

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Informed consent was obtained from all individual participants included in the study.

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The authors declare no competing interests.

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Highlights

1.The enzymatic asymmetric hydrogenation of C = C bonds was investigated with a SpinChem reactor.

2.The asymmetric hydrogenation of C = C binds had an excellent performance in the SpinChem reactor.

3.The immobilized enzymes have a longer useful life in SpinChem reactor than that in other reactors.

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Ma, T., Kong, W., Liu, Y. et al. Asymmetric Hydrogenation of C = C Bonds in a SpinChem Reactor by Immobilized Old Yellow Enzyme and Glucose Dehydrogenase. Appl Biochem Biotechnol 194, 4999–5016 (2022). https://doi.org/10.1007/s12010-022-03991-9

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