Platform for Multiple Isotope Labeling via Carbon-Sulfur Bond Exchange.

J Am Chem Soc

Université Paris-Saclay, CEA, Service de Chimie Bio-organique et Marquage, DMTS, F-91191 Gif-sur-Yvette, France.

Published: March 2024

AI Article Synopsis

  • The study presents a novel nickel-catalyzed method for reversible activation of carbon-sulfur (C-S) bonds, allowing for selective sulfur isotope exchange.
  • Isotope labeling is crucial in life sciences, particularly for nuclear imaging and understanding drug behavior, but current methods are limited and often specific to certain elements.
  • This new approach supports multiple isotopes (like deuterium and carbon-14) for labeling a variety of organic molecules, including pharmaceuticals, and offers potential for improved isotopic encryption.

Article Abstract

In this work, we explore a nickel-catalyzed reversible carbon-sulfur (C-S) bond activation strategy to achieve selective sulfur isotope exchange. Isotopes are at the foundation of applications in life science, such as nuclear imaging, and are essential tools for the determination of pharmacokinetic and dynamic profiles of new pharmaceuticals. However, the insertion of an isotope into an organic molecule remains challenging, and current technologies are element-specific. Despite the ubiquitous presence of sulfur in many biologically active molecules, sulfur isotope labeling is an underexplored field, and sulfur isotope exchange has been overlooked. This approach enables us to move beyond standardized element-specific procedures and was applied to multiple isotopes, including deuterium, carbon-13, sulfur-34, and radioactive carbon-14. These results provide a unique platform for multiple isotope labeling and are compatible with a wide range of substrates, including pharmaceuticals. In addition, this technology proved its potential as an isotopic encryption device for organic molecules.

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http://dx.doi.org/10.1021/jacs.3c14106DOI Listing

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