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Synthesis of optically active deuterium‐labeled homocysteine thiolactone
Author(s) -
Shinohara Yoshihiko,
Hasegawa Hiroshi,
Hashimoto Takao,
Ichida Kimiyoshi
Publication year - 2010
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1782
Subject(s) - thiolactone , chemistry , diastereomer , amide , stereochemistry , hydrolysis , column chromatography , hydrochloride , organic chemistry
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.