Enantioselective synthesis of D- and L-α-methylcysteine with hydantoinase

被引：10
|
作者：
Ohishi, Takahiro
Nanba, Hirokazu
Sugawara, Masanobu
Izumida, Masashi
Honda, Tatsuya
Mori, Kohei
Yanagisawa, Satohiro
Ueda, Makoto
Nagashima, Nobuo
Inoue, Kenji
机构：
[1] KANEKA Corp, Frontier Mat Dev Labs, Frontier Mat R&D Ctr, Corp Res & Dev Div, Osaka 5660072, Japan
[2] KANEKA Corp, Fine Chem Div, Fine Chem Res Lab, Takasago, Hyogo 6768688, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 19期
关键词：
enantioselective synthesis; alpha-methylcysteine; hydantoinase; tert-Butyl group; scalable process;
D O I：
10.1016/j.tetlet.2007.03.040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A scalable and cost-effective synthesis of D- and L-alpha-methylcysteine is described. A key step is D-selective cyclization of N-carbamoyl S-tert-butyl-D,L-alpha-methylcysteine catalyzed by hydantoinase. D-5-tert-Butylthiomethyl-5-methylhydantoin and A-carbamoyl S-tert-butyl-L-alpha-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-ot-methylcysteine hydrochloride were obtained. (c) 2007 Elsevier Ltd. All rights reserved.
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页码：3437 / 3440
页数：4
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