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Photobiocatalytic Platform for the Efficient Enantio-Divergent Synthesis of β-Fluoromethylated Ketones

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    Photobiocatalytic Platform for the Efficient Enantio-Divergent Synthesis of β-Fluoromethylated Ketones
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    • Yuan-Yang Guo*
      Yuan-Yang Guo
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      *Email: [email protected]
      More by Yuan-Yang Guo
      Orcidhttps://orcid.org/0000-0003-2034-7792
    • Ze-Hua Tian
      Ze-Hua Tian
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Ze-Hua Tian
    • Linghong Zhang
      Linghong Zhang
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Linghong Zhang
    • Yu-Chen Han
      Yu-Chen Han
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Yu-Chen Han
    • Bei-Bei Zhang
      Bei-Bei Zhang
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Bei-Bei Zhang
    • Qing Xing
      Qing Xing
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Qing Xing
    • Tianju Shao
      Tianju Shao
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Tianju Shao
    • Yang Liu
      Yang Liu
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      More by Yang Liu
    • Zhiyong Jiang*
      Zhiyong Jiang
      State Key Laboratory of Antiviral Drugs; Collaborative Innovation Centre of Henan Province for Green Manufacturing of Fine Chemicals; Key Laboratory of Green Chemical Media and Reactions, Ministry of Education; NMPA Key Laboratory for Research and Evaluation of Innovative Drug; Henan Key Laboratory of Organic Functional Molecule and Drug Innovation; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
      *Email: [email protected]
      More by Zhiyong Jiang
    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 45, 31012–31020
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c10441
    Published October 29, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    β-Fluoromethyl (CH2F, CHF2, and CF3)-substituted chiral ketones are essential moieties and are vital building blocks in pharmaceutical and agrochemistry. However, general and convenient methods for enantio-diverse access to diverse β-fluoromethylated ketones are lacking, hindering the further development of these functional moieties. In this study, we developed an ene-reductase-based photobiocatalytic platform for efficient synthesis of enantio-divergent β-fluoromethylated chiral ketones. Our method highlights substrate-type diversity, excellent enantioselectivity, enzymatic enantio-divergent synthesis, as well as a dicyanopyrazine (DPZ)-type photosensitizer for biocompatible olefin E/Z isomerization in enzymatic stereoconvergent olefin asymmetric reduction, thereby providing a general photobiocatalytic solution to diverse β-fluoromethylated chiral ketones.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.4c10441.

    • General experimental methods; protein design and purification; enzyme engineering; substrate synthesis; chemical characterization; NMR spectra (PDF)

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    Cited By

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    This article is cited by 2 publications.

    1. Jinhai Yu, Bin Chen, Xiaoqiang Huang. Single‐Electron Oxidation Triggered by Visible‐Light‐Excited Enzymes for Asymmetric Biocatalysis. Angewandte Chemie 2024, 2 https://doi.org/10.1002/ange.202419262
    2. Jinhai Yu, Bin Chen, Xiaoqiang Huang. Single‐Electron Oxidation Triggered by Visible‐Light‐Excited Enzymes for Asymmetric Biocatalysis. Angewandte Chemie International Edition 2024, 4 https://doi.org/10.1002/anie.202419262
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 45, 31012–31020
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c10441
    Published October 29, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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