Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-(2-earboxyethylthio)propanoic Acid

Abstract

Electrophilic additions of dl- and l-Cys to propenoic acid afforded (RS)- and (R)-2-amino-3-(2-carboxy-ethylthio)propanoic acids [(RS)- and (R)-ACE], respectively. (RS)-ACE was found to exist as a conglomerate based on its melting point, solubility, and infrared spectrum. (RS)-ACE was optically resolved by preferential crystallization to yield (R)- and (S)ACE. The obtained (R)- and (S)-ACE were efficiently recrystallized from water, taking account of the solubility of (RS)-ACE, to give them in optically pure form. © 1998, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.