Base-promoted dynamic amide exchange: efficient access to isotopically enriched tertiary amides
Amide isotope labeling is a crucial tool in drug discovery and development. However, current methods label the desired peptide bond in a multi-step fashion. This study presents novel strategies for amide isotope exchange through transamidation and amide metathesis. By optimizing reaction conditions and exploring substrate scope, we achieved direct labeling of both amine and carbonyl moieties. These findings pave the way for more sustainable isotope labeling technologies. Furthermore, preliminary examples of isotope-containing waste recycling demonstrate a crucial step towards a greener future for isotope chemistry.
Authors
- Davide Audisio (ORCID: https://orcid.org/0000-0002-6234-3610)
- Frédéric Taran (ORCID: https://orcid.org/0000-0001-5461-329X)
- Antoine Sallustrau (ORCID: https://orcid.org/0000-0001-7118-9224)
- Timothée D’Anfray
- Rémi Blieck (ORCID: https://orcid.org/0000-0001-5100-5934)
- Quentin Lemesre (ORCID: https://orcid.org/0000-0003-1343-8477)
Institutions
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Université Paris-Saclay (FR)
- CEA Paris-Saclay (FR)
- Institut de Biologie et Technologies (FR)
Publication Details
- Journal
- Chemical Science
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5sc02566d
- Citations
- 2
- Primary Topic
- Advanced Synthetic Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- European Commission
- Agence Nationale de la Recherche
- European Research Council