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Synthesis of optically active deuterium-labeled homocysteine thiolactone

✍ Scribed by Yoshihiko Shinohara; Hiroshi Hasegawa; Takao Hashimoto; Kimiyoshi Ichida

Publisher
John Wiley and Sons
Year
2010
Tongue
French
Weight
241 KB
Volume
53
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Optically pure (R)‐ and (S)‐3‐aminotetradeutero‐2‐thiophenone (D‐ and L‐[^2^H~4~]homocysteine thiolactone) for use as substrates for metabolic and pharmacokinetic studies has been prepared. The racemic [^2^H~4~]homocysteine thiolactone hydrochloride was prepared from commercially available and highly enriched DL‐[3,3,4,4‐^2^H~4~]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‐[^2^H~4~]homocysteine thiolactone, respectively. Copyright © 2010 John Wiley & Sons, Ltd.

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