Enantioselective synthesis of d- and l-α-methylcysteine with hydantoinase

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 o...

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Bibliographic Details
Published in:Tetrahedron letters 2007-05, Vol.48 (19), p.3437-3440
Main Authors: Ohishi, Takahiro, Nanba, Hirokazu, Sugawara, Masanobu, Izumida, Masashi, Honda, Tatsuya, Mori, Kohei, Yanagisawa, Satohiro, Ueda, Makoto, Nagashima, Nobuo, Inoue, Kenji
Format: Article
Language:English
Subjects:
Enantioselective synthesis
Hydantoinase
Scalable process
tert-Butyl group
α-Methylcysteine
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.03.040