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.

引用

页码：3437 / 3440

页数：4

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