Synthesis of D- and L-selenomethionine double-labeled with deuterium and selenium-82.
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-[²H₃, ⁸²Se]selenomethionine were prepared by condensation of (R)- and (S)-2-amino-4-bromobutylic acid with lithium [²H₃, ⁸²Se]methaneselenolate, which was prepared from metal (82)Se 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.
Juntendo University School of Medicine, Bunkyo-ku, Tokyo, Japan. tmatsuka@juntendo.ac.jp
Takehisa
T
Matsukawa
Hiroshi
H
Hasegawa
Yoshihiko
Y
Shinohara
Jun
J
Kobayashi
Atsuko
A
Shinohara
Momoko
M
Chiba
Kimiyoshi
K
Ichida
Kazuhito
K
Yokoyama
D002851:Chromatography, High Pressure Liquid; D003903:Deuterium / Q000737:chemistry*; D007553:Isotope Labeling; D007554:Isotopes / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*; D012645:Selenomethionine / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007554:Isotopes; D012645:Selenomethionine; D003903:Deuterium; D012643:Selenium