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)

1 LMC - Laboratoire de Marquage au Carbone 14
2 IMIV - U1023 - ERL9218 - Imagerie Moléculaire in Vivo
3 LTMB2 - LTMB équipe 2

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.

Keywords: Carbon dioxide; carbon-11; Late-stage isotopic labeling; carbon-14; Heterocycles

Domains: Chemical Sciences

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, 2018, ⟨10.1002/anie.201804838⟩. ⟨cea-01818428⟩