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Shiraiwa T, Tadokoro K, Tanaka H, et al. Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride. Biosci Biotechnol Biochem. 1998;62(12):2382-7doi: 10.1271/bbb.62.2382.
Shiraiwa, T., Tadokoro, K., Tanaka, H., Nanba, K., Yokono, N., Shibazaki, K., Kubo, M., & Kurokawa, H. (1998). Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride. Bioscience, biotechnology, and biochemistry, 62(12), 2382-7. https://doi.org/10.1271/bbb.62.2382
Shiraiwa, T, et al. "Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride." Bioscience, biotechnology, and biochemistry vol. 62,12 (1998): 2382-7. doi: https://doi.org/10.1271/bbb.62.2382
Shiraiwa T, Tadokoro K, Tanaka H, Nanba K, Yokono N, Shibazaki K, Kubo M, Kurokawa H. Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride. Biosci Biotechnol Biochem. 1998;62(12):2382-7. doi: 10.1271/bbb.62.2382. PMID: 27392398.
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Biosci Biotechnol Biochem. 1998;62(12):2382-7. doi: 10.1271/bbb.62.2382.

Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride.

Bioscience, biotechnology, and biochemistry

T Shiraiwa, K Tadokoro, H Tanaka, K Nanba, N Yokono, K Shibazaki, M Kubo, H Kurokawa

Affiliations

  1. a Chemical Branch, Faculty of Engineering and Kansai University High Technology Research Center, Kansai University.

PMID: 27392398 DOI: 10.1271/bbb.62.2382

Abstract

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 hydrochlo-ride [(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•HCl in ethanol in the presence of triethylamine.

Keywords: 1,4-thiazane-3-carboxylic acid; 2-amino-3-[(2-chloroethyl)sulfanyl]propanoic acid hydrochloride; conglomerate; optical resolution; preferential crystallization

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