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Hydrogen Isotope Labeling of Pharmaceuticals Via Dual Hydrogen Isotope Exchange Pathways Using CdS Quantum Dot Photocatalyst

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2024, 146, 49, 34141-34151
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    Hydrogen Isotope Labeling of Pharmaceuticals Via Dual Hydrogen Isotope Exchange Pathways Using CdS Quantum Dot Photocatalyst
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    • Rajendra Maity
      Rajendra Maity
      Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112, United States
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    • Otto Dungan
      Otto Dungan
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
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      Orcidhttps://orcid.org/0009-0007-9426-4611
    • Frédéric A. Perras
      Frédéric A. Perras
      Chemical and Biological Sciences Division, Ames National Laboratory, Ames, Iowa 50011, United States
      Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States
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    • Jingwei Li*
      Jingwei Li
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
      *Email: [email protected]
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    • Daohua Liu
      Daohua Liu
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
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    • Sumei Ren
      Sumei Ren
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
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      Orcidhttps://orcid.org/0000-0002-5163-0489
    • Dan Lehnherr
      Dan Lehnherr
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
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      Orcidhttps://orcid.org/0000-0001-8392-1208
    • Zheng Huang
      Zheng Huang
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
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      Orcidhttps://orcid.org/0000-0003-0876-5369
    • Eric M. Phillips
      Eric M. Phillips
      Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States
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      Orcidhttps://orcid.org/0000-0003-3530-8876
    • Moses Adeyemo
      Moses Adeyemo
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
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      Orcidhttps://orcid.org/0000-0002-0493-3145
    • Joseph Frimpong
      Joseph Frimpong
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
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    • Timothy Quainoo
      Timothy Quainoo
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
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    • Zhen-Fei Liu
      Zhen-Fei Liu
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
      More by Zhen-Fei Liu
      Orcidhttps://orcid.org/0000-0002-2423-8430
    • Long Luo*
      Long Luo
      Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112, United States
      Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, United States
      *Email: [email protected]
      More by Long Luo
      Orcidhttps://orcid.org/0000-0001-5771-6892
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 49, 34141–34151
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c13857
    Published November 23, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    Isotopic labeling is a powerful technique extensively used in the pharmaceutical industry. By tracking isotope-labeled molecules, researchers gain unique and invaluable insights into the pharmacokinetics and pharmacodynamics of new drug candidates. Hydrogen isotope labeling is particularly important as hydrogen is ubiquitous in organic molecules in biological systems, and it can be introduced effectively through late-stage hydrogen isotope exchange (HIE). However, hydrogen isotope methods that simultaneously label multiple sites with varying types of C–H bonds in the different types of molecules are still lacking. Herein, we demonstrate a heterogeneous photocatalytic system using a CdS quantum dot catalyst that proceeds via a unique dual HIE pathway mechanism─one occurs in the reaction solution and the other on the catalytic surface─to address it. This unique mechanism unlocked several unique labeling capabilities, including simultaneous labeling of multiple and challenging sites such as secondary α-amino, α-ethereal, allyl, and vinyl sites, providing great versatility in practical uses for pharmaceutical labeling.

    Copyright © 2024 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.4c13857.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 49, 34141–34151
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c13857
    Published November 23, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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