Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, D-18059 Rostock, Germany.
J Am Chem Soc. 2012 Jul 25;134(29):12239-44. doi: 10.1021/ja3041338. Epub 2012 Jul 12.
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.
一种新颖、简便的利用 borrow hydrogen 方法催化生物活性叔胺的氘氢交换的方法已经被开发出来。在易得的 Shvo 催化剂存在下，实现了对α-和β-质子相对于氮原子的优异化学选择性，以及高氘掺入度和官能团容忍度。这使得复杂的药物相关底物的氘化成为可能，包括实际上市药物化合物的例子。值得注意的是，该方法为各种生命科学应用中对 LC-MS/MS 分析高度需求的有价值的内标材料的生成提供了有力工具。
