Preparations of Optically Active Homocysteine and Homocystine by Asymmetric Transformation of (RS)-1, 3-Thiazane-4-carboxylic Acid.

H Miyazaki, A Ohta, N Kawakatsu, Y Waki…

Index: Miyazaki, Hideya; Ohta, Atsushi; Kawakatsu, Nobuyuki; Waki, Yukitaka; Gogun, Yasuhiro; et al. Bulletin of the Chemical Society of Japan, 1993 , vol. 66, # 2 p. 536 - 540

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Citation Number: 19

Abstract

DL-Homocysteine [DL-Hcy] from (RS)-homocysteine thiolactone hydrochloride [(RS)-HTL· HCl] was subjected to reaction with formaldehyde in acetic acid to give (RS)-1, 3-thiazane-4- carboxylic acid monohydrate [(RS)-THA· H 2 O]. An asymmetric transformation of (RS)-THA· H 2 O was achieved via salt formation with optically active tartaric acid in the presence of salicylaldehyde in acetic acid. The (R)-and (S)-THA obtained, respectively, from the salt of ...