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Enantioselective synthesis of d- and l-α-methylcysteine with hydantoinase |
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| Authors: | Takahiro Ohishi Hirokazu Nanba Masashi Izumida Kohei Mori Makoto Ueda Kenji Inoue |
| Affiliation: | a Frontier Materials Development Laboratories, Frontier Materials R&D Center, Corporate Research and Development Division, KANEKA Corporation, 5-1-1, Torikai-Nishi, Settsu, Osaka 566-0072, Japan b Fine Chemicals Research Laboratories, Fine Chemicals Division, KANEKA Corporation, 1-8, Miyamae-machi, Takasago-cho, Takasago, Hyogo 676-8688, Japan |
| Abstract: | A scalable and cost-effective synthesis of d- and l-α-methylcysteine is described. A key step is d-selective cyclization of N-carbamoyl S-tert-butyl-d,l-α-methylcysteine catalyzed by hydantoinase. d-5-tert-Butylthiomethyl-5-methylhydantoin and N-carbamoyl S-tert-butyl-l-α-methylcysteine were obtained with excellent yield and optical purity, and these compounds were easily separated by filtration. After hydrolysis and cleavage of the tert-butyl group, d- and l-α-methylcysteine hydrochloride were obtained. |
| Keywords: | Enantioselective synthesis α-Methylcysteine Hydantoinase tert-Butyl group Scalable process |
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