Pyridine-based strategies towards nitrogen isotope exchange and multiple isotope incorporation.
Nat Commun, 2024/7/18;15(1):6063.
Feng M[1], Norlöff M[1], Guichard B[1], Kealey S[2], D'Anfray T[1], Thuéry P[3], Taran F[1], Gee A[2], Feuillastre S[4], Audisio D[5]
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PMID: 39025881DOI: 10.1038/s41467-024-50139-w
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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.
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