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Late-stage isotopic carbon labeling of pharmaceutically relevant cyclic ureas directly from CO2

Antonio del Vecchio 1 Fabien Caillé 2 Arnaud Chevalier 1 Olivier Loreau 1 Kaisa Horkka Christer Halldin Magnus Schou Nathalie Camus 1 Pascal Kessler 3 Bertrand Kuhnast 2 Frédéric Taran 1 Davide Audisio 1, *
* Corresponding author
1 LMC - Laboratoire de Marquage au Carbone 14
SCBM - Service de Chimie Bio-Organique et de Marquage : DRF/JOLIOT
3 LTMB2 - LTMB équipe 2
SIMoS - Service d'Ingénierie Moléculaire pour la Santé (ex SIMOPRO) : DRF/JOLIOT
Abstract : A robust, click chemistry inspired procedure for radiolabeling of cyclic ureas was developed. This protocol, suitable for all carbon isotopes (11C, 13C, 14C), is based on the direct functionalization of carbon dioxide: the universal building block for carbon radiolabeling. The strategy is operationally simple, reproducible in different radiochemistry centers, exhibits a remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity compared to previously reported systems. With this procedure, a variety of pharmaceuticals and an unprotected peptide were labeled with high radiochemical efficiency.
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Submitted on : Monday, August 6, 2018 - 4:51:08 PM
Last modification on : Thursday, August 20, 2020 - 5:11:37 PM
Long-term archiving on: : Wednesday, November 7, 2018 - 5:41:49 PM

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Antonio del Vecchio, Fabien Caillé, Arnaud Chevalier, Olivier Loreau, Kaisa Horkka, et al.. Late-stage isotopic carbon labeling of pharmaceutically relevant cyclic ureas directly from CO2. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2018, ⟨10.1002/anie.201804838⟩. ⟨cea-01818428⟩

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