Bioscience, Biotechnology and Biochemistry p. 2382 - 2387 (1998)
Update date:2022-08-04
Topics:
Shiraiwa, Tadashi
Tadokoro, Kohya
Tanaka, Haruyuki
Nanba, Keiichiro
Yokono, Noriyoshi
Shibazaki, Katsuyoshi
Kubo, Motoki
Kurokawa, Hidemoto
Optically active 1,4-thiazane-3-carboxylic acid [TCA] was synthesized from cysteine via optical resolution by preferential crystallization. The intermediate (RS)-2-amino-3-[(2-chloroethyl)sulfanyl]propanoic acid hydrochloride [(RS)-ACS-HCl] was found to exist as a conglomerate based on its melting point, solubility and IR spectrum. (RS)-ACS·HCl was optically resolved by preferential crystallization to yield (R)- and (S)-ACS·HCl. (R)- and (S)-ACS·HCl thus obtained were recrystallized from a mixture of hydrochloric acid and 2-propanol, taking account of the solubility of (RS)-ACS·HCl, efficiently yielding both enantiomers in optically pure forms. (R)- and (S)-TCA were then respectively synthesized by the cyclization of (R)- and (S)-ACS·HCI in ethanol in the presence of triethylamine.
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