Y. Shinohara, H. Hasegawa, T. Hashimoto
Jun 30, 2010
Citations
0
Influential Citations
2
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
Optically pure (R)- and (S)-3-aminotetradeutero-2-thiophenone (D- and L-[2H4]homocysteine thiolactone) for use as substrates for metabolic and pharmacokinetic studies has been prepared. The racemic [2H4]homocysteine thiolactone hydrochloride was prepared from commercially available and highly enriched DL-[3,3,4,4-2H4]methionine by intramolecular condensation with hydriodic acid. The racemate was derivatized with (S)-(+)-2-methoxyphenylacetic acid to form the diastereomeric amides. The diastereomers were separated by silica gel column chromatography. Hydrolysis of the D- and L-isomer amide in 4 M HCl–ethanol (1:2 v/v) afforded the optically pure D- and L-[2H4]homocysteine thiolactone, respectively. Copyright © 2010 John Wiley & Sons, Ltd.