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Regioselective and Stereospecific Deuteration of Bioactive Aza Compounds by the Use of Ruthenium Nanoparticles

Authors

  • Dr. Grégory Pieters,

    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
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  • Céline Taglang,

    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
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  • Dr. Eric Bonnefille,

    1. CNRS; LCC (Laboratoire de Chimie de Coordination), 205, Route de Narbonne, 31077 Toulouse (France)
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  • Dr. Torsten Gutmann,

    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
    2. Current address: Eduard Zintl Institute for Inorganic and Physical Chemistry, Technical University Darmstadt, Petersenstrasse 20, 64287 Darmstadt (Germany)
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  • Céline Puente,

    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
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  • Dr. Jean-Claude Berthet,

    1. CEA Saclay, IRAMIS, SIS2M, CNRS UMR 3299, 91191 Gif-sur-Yvette (France)
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  • Dr. Christophe Dugave,

    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
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  • Dr. Bruno Chaudret,

    Corresponding author
    1. LPCNO (Laboratoire de Physique et Chimie de Nano-Objets), UMR 5215 INSA-CNRS-UPS, Institut National des Sciences Appliquées, 135, Avenue de Rangueil, 31077 Toulouse (France)
    • Bruno Chaudret, LPCNO (Laboratoire de Physique et Chimie de Nano-Objets), UMR 5215 INSA-CNRS-UPS, Institut National des Sciences Appliquées, 135, Avenue de Rangueil, 31077 Toulouse (France)

      Bernard Rousseau, CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)

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  • Dr. Bernard Rousseau

    Corresponding author
    1. CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)
    • Bruno Chaudret, LPCNO (Laboratoire de Physique et Chimie de Nano-Objets), UMR 5215 INSA-CNRS-UPS, Institut National des Sciences Appliquées, 135, Avenue de Rangueil, 31077 Toulouse (France)

      Bernard Rousseau, CEA Saclay, SCBM, iBiTec-S, Building 547, PC # 108, 91191 Gif sur Yvette (France)

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  • Support from ERC Ternanomed is acknowledged.

Abstract

An efficient H/D exchange method allowing the deuteration of pyridines, quinolines, indoles, and alkyl amines with D2 in the presence of Ru@PVP nanoparticles is described. By a general and simple procedure involving mild reaction conditions and simple filtration to recover the labeled product, the isotopic labeling of 22 compounds proceeded in good yield with high chemo- and regioselectivity. The viability of this procedure was demonstrated by the labeling of eight biologically active compounds. Remarkably, enantiomeric purity was conserved in the labeled compounds, even though labeling took place in the vicinity of the stereogenic center. The level of isotopic enrichment observed is suitable for metabolomic studies in most cases. This approach is also perfectly adapted to tritium labeling because it uses a gas as an isotopic source. Besides these applications to molecules of biological interest, this study reveals a rich and underestimated chemistry on the surface of ruthenium nanoparticles.

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