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
收藏
页码：3437 / 3440
页数：4
相关论文
共 50 条
  • [31] Design and Synthesis of Orthogonally Protected D- and L-β-Hydroxyenduracididines from D-lyxono-1,4-Lactone
    Lin, Cheng-Kun
    Hou, Chung-Chien
    Guo, Yi-Yong
    Cheng, Wei-Chieh
    ORGANIC LETTERS, 2016, 18 (20) : 5216 - 5219
  • [32] REDUCTION OF CHOLESTEROL ABSORPTION IN HAMSTERS WITH D- AND L- THYROXINE ADMINISTRATION
    HENDERSO.DH
    FELDMAN, EB
    FEDERATION PROCEEDINGS, 1969, 28 (02) : 687 - &
  • [33] 从L-色氨酸制备D-色氨酸
    韦平和
    彭加平
    周锡樑
    中国医药工业杂志, 2013, (08) : 752 - 753
  • [34] About d-, l- and r- protein cystin.
    Neuberg, C
    Mayer, P
    HOPPE-SEYLERS ZEITSCHRIFT FUR PHYSIOLOGISCHE CHEMIE, 1905, 44 (5/6): : 498 - 510
  • [35] Protein Design with L- and D-α-Amino Acid Structures as the Alphabet
    Durani, Susheel
    ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (10) : 1301 - 1308
  • [36] L-薄荷基-β-D-乳糖苷的合成
    卢高超
    陈朗秋
    唐秋娥
    刘灯峰
    李宏伟
    陈丽
    食品科学 , 2013, (04) : 83 - 87
  • [37] A calorimetric study of L-, D- and DL-isomers of tryptophan
    Gheorghe, Daniela
    Neacsu, Ana
    Contineanu, Iulia
    Tanasescu, Speranta
    Perisanu, Stefan
    JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2017, 130 (02) : 1145 - 1152
  • [38] Cocaine and κ-opioid withdrawal in Planaria blocked by D-, but not L-, glucose
    Umeda, S
    Stagliano, GW
    Raffa, RB
    BRAIN RESEARCH, 2004, 1018 (02) : 181 - 185
  • [39] Both the D-(+) and L-(-) enantiomers of nicotine inhibit Aβ aggregation and cytotoxicity
    Moore, SA
    Huckerby, TN
    Gibson, GL
    Fullwood, NJ
    Turnbull, S
    Tabner, BJ
    El-Agnaf, OMA
    Allsop, D
    BIOCHEMISTRY, 2004, 43 (03) : 819 - 826
  • [40] Analysis of Selected and Designed Chimeric D- and L-α-Helix Assemblies
    Kuekenshoener, Tim
    Hagemann, Urs B.
    Wohlwend, Daniel
    Raeuber, Christina
    Baumann, Tobias
    Keller, Sandro
    Einsle, Oliver
    Mueller, Kristian M.
    Arndt, Katja M.
    BIOMACROMOLECULES, 2014, 15 (09) : 3296 - 3305
12345