Pyridine-based strategies towards nitrogen isotope exchange and multiple isotope incorporation

Minghao Feng, Maylis Norlöff, Benoit Guichard, Steven Kealey, Timothée D’Anfray, Pierre Thuéry, Frédéric Taran, Antony Gee, Sophie Feuillastre () and Davide Audisio ()
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Minghao Feng: DMTS
Maylis Norlöff: DMTS
Benoit Guichard: DMTS
Steven Kealey: St Thomas’ Hospital
Timothée D’Anfray: DMTS
Pierre Thuéry: NIMBE
Frédéric Taran: DMTS
Antony Gee: St Thomas’ Hospital
Sophie Feuillastre: DMTS
Davide Audisio: DMTS

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Isotopic labeling is at the core of health and life science applications such as nuclear imaging, metabolomics and plays a central role in drug development. The rapid access to isotopically labeled organic molecules is a sine qua non condition to support these societally vital areas of research. Based on a rationally driven approach, this study presents an innovative solution to access labeled pyridines by a nitrogen isotope exchange reaction based on a Zincke activation strategy. The technology conceptualizes an opportunity in the field of isotope labeling. 15N-labeling of pyridines and other relevant heterocycles such as pyrimidines and isoquinolines showcases on a large set of derivatives, including pharmaceuticals. Finally, we explore a nitrogen-to-carbon exchange strategy in order to access 13C-labeled phenyl derivatives and deuterium labeling of mono-substituted benzene from pyridine-2H5. These results open alternative avenues for multiple isotope labeling on aromatic cores.

Date: 2024
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DOI: 10.1038/s41467-024-50139-w

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