Synthesis of D- and L-selenomethionine double-labeled with deuterium and selenium-82

The synthesis of D- and L-selenomethionine labeled with ?2Se and three deuteriums at Se-methyl group (D- and L-2H?, ?2Se]selenomethionine) was described. D- And L-2H?, ?2Se]selenomethionine were prepared by condensation of (R)- and (S)-2-amino-4-bromobutylic acid with lithium 2H?, ?2Se]methaneselenolate, which was prepared from metal (82)Se and 2H?]methyl iodide. The optical purities of D- and L-2H?, ?2Se]selenomethionine were determined by HPLC with a chiral stationary phase column and were found more than 99% ee. The chemical ionization mass spectra showed that the molecular related ion for N-isobutyloxycarbonyl ethyl ester derivatives of 2H?, ?2Se]selenomethionine did not overlap with the m/z values known from that of non-labeled selenomethionine.