Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen-Isotope Exchange

Alberto Palazzolo 1 Sophie Feuillastre 1, * Viktor Pfeifer 1 Sébastien Garcia-Argote 1 Donia Bouzouita 2 Simon Tricard 2 Celine Chollet 1 Elodie Marcon 1 David-Alexandre Buisson 1 Sophie Cholet 3 François Fenaille 3 Guy Lippens 4 Bruno Chaudret 2 Grégory Pieters 1
* Corresponding author
1 SCBM - Service de Chimie Bio-Organique et de Marquage
2 LPCNO - Laboratoire de physique et chimie des nano-objets
3 LEMM - Laboratoire d'Etude du Métabolisme des Médicaments
SPI - Service de Pharmacologie et Immunoanalyse : DRF/JOLIOT
4 LISBP - Laboratoire d'Ingénierie des Systèmes Biologiques et des Procédés
Abstract : A general approach for the efficient hydrogen-isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC-MS quantification.
Keywords : nucleotides nanoparticles C−H activation isotopes isotopic labelling
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Journal articles
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CEA | IRSAMC | INRA | INSA-TOULOUSE | LPCNO | LISBP | JOLIOT | DMTS | INSA-GROUPE | CEA-DRF | UNIV-TLSE3

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Alberto Palazzolo, Sophie Feuillastre, Viktor Pfeifer, Sébastien Garcia-Argote, Donia Bouzouita, et al.. Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen-Isotope Exchange. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2019, ⟨10.1002/anie.201813946⟩. ⟨cea-02075752⟩

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