Photoredox-catalyzed deuteration and tritiation of pharmaceutical compounds

Photoredox-catalyzed deuteration and tritiation of pharmaceutical compoundsByYong Yao Loh,Kazunori Nagao,Andrew J. Hoover,David Hesk,Nelo R. Rivera,Steven L. Colletti,Ian W. Davies,David W. C. MacMillanScience01 Dec 2017 : 1182-1187A light-promoted atom transfer protocol uses heavy water to isotopically label alkyl sites for drug metabolism studies.Deuterium- and tritium-labeled pharmaceutical compounds are pivotal diagnostic tools in drug discovery research, providing vital information about the biological fate of drugs and drug metabolites. Herein we demonstrate that a photoredox-mediated hydrogen atom transfer protocol can efficiently and selectively install deuterium (D) and tritium (T) at α-amino sp3 carbon-hydrogen bonds in a single step, using isotopically labeled water (D2O or T2O) as the source of hydrogen isotope. In this context, we also report a convenient synthesis of T2O from T2, providing access to high-specific-activity T2O. 

Source: Organometallic Current - December 1, 2017 Category: Chemistry Tags: Deuteration Photoredox Catalysis Source Type: blogs