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Hydrogen/Deuterium Transfer from Anisole to Methoxy Radicals: A Theoretical Study of a Deuterium-Labeled Drug Model

  • Yuka Kimura
    Yuka Kimura
    International College of Arts and Sciences, Yokohama City University, 22-2 Seto, Kanazawa, Yokohama 236-0027, Japan
    More by Yuka Kimura
  • Yusuke Kanematsu
    Yusuke Kanematsu
    Smart Innovation Program, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
    Division of Materials Model-Based Research, Digital Monozukuri (Manufacturing) Education and Research Center, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
  • Hiroki Sakagami
    Hiroki Sakagami
    Graduate School of Data Science, Yokohama City University, 22-2 Seto, Kanazawa, Yokohama 236-0027, Japan
  • David S. Rivera Rocabado
    David S. Rivera Rocabado
    Smart Innovation Program, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
  • Tomomi Shimazaki
    Tomomi Shimazaki
    Graduate School of Nanobioscience, Yokohama City University, 22-2 Seto, Kanazawa, Yokohama 236-0027, Japan
  • Masanori Tachikawa
    Masanori Tachikawa
    Graduate School of Data Science, Yokohama City University, 22-2 Seto, Kanazawa, Yokohama 236-0027, Japan
  • , and 
  • Takayoshi Ishimoto*
    Takayoshi Ishimoto
    Smart Innovation Program, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
    Division of Materials Model-Based Research, Digital Monozukuri (Manufacturing) Education and Research Center, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8527, Japan
    Graduate School of Nanobioscience, Yokohama City University, 22-2 Seto, Kanazawa, Yokohama 236-0027, Japan
    *Email: [email protected]
Cite this: J. Phys. Chem. A 2022, 126, 1, 155–163
Publication Date (Web):January 4, 2022
https://doi.org/10.1021/acs.jpca.1c08514
Copyright © 2022 American Chemical Society

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    Abstract

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    Recently, deuterium-labeled drugs, such as deutetrabenazine, have attracted considerable attention. Consequently, understanding the reaction mechanisms of deuterium-labeled drugs is crucial, both fundamentally and for real applications. To understand the mechanisms of H- and D-transfer reactions, in this study, we used deuterated anisole as a deutetrabenazine model and computationally considered the nuclear quantum effects of protons, deuterons, and electrons. We demonstrated that geometrical differences exist in the partially and fully deuterated methoxy groups and hydrogen-bonded structures of intermediates and transition states due to the H/D isotope effect. The observed geometrical features and electronic structures are ascribable to the different nuclear quantum effects of protons and deuterons. Primary and secondary kinetic isotope effects (KIEs) were calculated for H- and D-transfer reactions from deuterated and undeuterated anisole, with the calculated primary KIEs in good agreement with the corresponding experimental data. These results reveal that the nuclear quantum effects of protons and deuterons need to be considered when analyzing the reaction mechanisms of H- and D-transfer reactions and that a theoretical approach that directly includes nuclear quantum effects is a powerful tool for the analysis of H/D isotope effects in H- and D-transfer reactions.

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    Cited By

    This article is cited by 1 publications.

    1. Taro Udagawa, Ikumi Hattori, Yusuke Kanematsu, Takayoshi Ishimoto, Masanori Tachikawa. Nuclear quantum effect and H/D isotope effect in excited state intramolecular proton transfer and electron‐induced intramolecular proton transfer reactions in 8‐hydroxyquinoline. International Journal of Quantum Chemistry 2022, 122 (19) https://doi.org/10.1002/qua.26962

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