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

Abstract

The synthesis of D- and L-selenomethionine labeled with 82Se and three deuteriums at Se-methyl group (D- and L-[2H3, 82Se]selenomethionine) was described. D- And L-[2H 3, 82Se]selenomethionine were prepared by condensation of (R)- and (S)-2-amino-4-bromobutylic acid with lithium [2H 3, 82Se]methaneselenolate, which was prepared from metal 82Se and [2H3]methyl iodide. The optical purities of D- and L-[2H3, 82Se] 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 [2H3, 82Se]selenomethionine did not overlap with the m/z values known from that of non-labeled selenomethionine. © 2010 Pharmaceutical Society of Japan.