Ruthenium-Catalyzed Selective α,β-Deuteration of Bioactive Amines
| Autor: | Jens Atzrodt, Lorenz Neubert, Sebastian Imm, Wolfgang Holla, Matthias Beller, Volker Derdau, Helfried Neumann, Sebastian Bähn, Dirk Michalik |
|---|---|
| Rok vydání: | 2012 |
| Předmět: |
Shvo catalyst
Borrowing hydrogen Deuterium Exchange Measurement chemistry.chemical_element General Chemistry Deuterium Biochemistry Ruthenium Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Pharmaceutical Preparations chemistry Tandem Mass Spectrometry Functional group Organic chemistry Amines Chemoselectivity Hydrogen |
| Zdroj: | Journal of the American Chemical Society. 134:12239-12244 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja3041338 |
| Popis: | A novel and convenient protocol for the catalytic hydrogen-deuterium exchange of biologically active tertiary amines utilizing the borrowing hydrogen methodology has been developed. In the presence of the readily available Shvo catalyst, excellent chemoselectivity toward α- and β-protons with respect to the nitrogen atom as well as high degree of deuterium incorporation and functional group tolerance is achieved. This allowed for the deuteration of complex pharmaceutically interesting substrates, including examples for actual marketed drug compounds. Notably, this method constitutes a powerful tool for the generation of valuable internal standard materials for LC-MS/MS analyses highly demanded for various life-science applications. |
| Databáze: | OpenAIRE |
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