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

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. Bas...

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Veröffentlicht in:Nature communications 2024-07, Vol.15 (1), p.6063-9, Article 6063
Hauptverfasser: Feng, Minghao, Norlöff, Maylis, Guichard, Benoit, Kealey, Steven, D’Anfray, Timothée, Thuéry, Pierre, Taran, Frédéric, Gee, Antony, Feuillastre, Sophie, Audisio, Davide
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Sprache:eng
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Zusammenfassung: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. 15 N-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 13 C-labeled phenyl derivatives and deuterium labeling of mono-substituted benzene from pyridine- 2 H 5 . These results open alternative avenues for multiple isotope labeling on aromatic cores. The rapid access to isotopically labeled organic molecules is a sine qua non condition to support these societally vital areas of research. Here the authors present a solution to access labeled pyridines by a nitrogen isotope exchange reaction based on a Zincke activation strategy.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-024-50139-w