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- Title
Photoredox‐Mediated Hydrogen Isotope Exchange Reactions of Amino‐Acids, Peptides, and Peptide‐Derived Drugs.
- Authors
Legros, Fabien; Fernandez‐Rodriguez, Patricia; Mishra, Anurag; Weck, Remo; Bauer, Armin; Sandvoss, Martin; Ruf, Sven; Méndez, María; Mora‐Radó, Helena; Rackelmann, Nils; Pöverlein, Christoph; Derdau, Volker
- Abstract
Hydrogen isotopically labelled compounds are essential diagnostic tools in drug research and development, as they provide vital information about the biological metabolism of drug candidates and their metabolites. Herein we report a photoredox‐initiated hydrogen atom transfer (HAT) protocol which efficiently and selectively introduces deuterium or tritium at C(sp3)−H bonds, utilizing heavy water (D2O or T2O) as the hydrogen isotope source, and a guanidine base. This protocol has been successfully applied to the incorporation of deuterium in several amino acids (lysine, glycine and proline) and small peptides. Finally, the method has been applied to tritium, because tritium‐labelled peptides are essential for application in biological experiments, such as ligand‐binding assays, or absorption, distribution, metabolism, and excretion (ADME) studies.
- Subjects
HYDROGEN isotopes; ISOTOPE exchange reactions; DEUTERIUM oxide; ABSTRACTION reactions; PEPTIDES; DRUG metabolism; TRITIUM; DEUTERIUM
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 56, p12738
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202003464