Stereoselective synthesis of d4-(S)-Lysine from (S)-Serine
Tetradeuterated (S)-lysine can easily be obtained from protected (S)-serine in a few steps including a Cu-mediated cross coupling and subsequent platinum-catalysed deuteration.
Kohr, Michael,Kazmaier, Uli
p. 4690 - 4694
(2019/02/01)
Synthesis of - and Lysines
Starting from readily available cyclohexanone (1), synthesis of the title - and lysines (11) and (18) is described.Although direct incorporation of an amino or phthalimide group into the 2-bromohexanoic acid (5), which was derived from 1 in five steps. leading to 11 was unsuccessful due to hydrogen-deuterium scrambling, compound (11) was obtained in 86percent deuterium content via incorporation of an azido group and subsequent hydrogenation.Furthermore, compound (18) having 99percent deuterium content could be prepared by acid-catalysed deuterium exchange of 1 as a key-step.