DPAMPP in catalytic asymmetric reactions: enantioselective synthesis of L-homophenylalanine

被引:32
|
作者
Xie, YN [1 ]
Lou, RL [1 ]
Li, Z [1 ]
Mi, AQ [1 ]
Jiang, YH [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(00)00092-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
L-Homophenylalanine 1, a key intermediate of most commercially important ACE inhibitors, was prepared via catalytic asymmetric hydrogenation of (Z)-2-acetamido-4-phenylcrotonate 3a with a cationic rhodium complex of(1 R,2S)-DPAMPP, followed by acid-hydrolysis of the protecting groups in good yield with >99.9% enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1487 / 1494
页数:8
相关论文
共 50 条
  • [1] Synthesis of L-homophenylalanine with immobilized enzymes
    Yen, Min-Chih
    Hsu, Wen-Hwei
    Lin, Sung-Chyr
    PROCESS BIOCHEMISTRY, 2010, 45 (05) : 667 - 674
  • [2] Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor
    Ahmad, A. L.
    Oh, P. C.
    Shukor, S. R. Abd
    BIOTECHNOLOGY ADVANCES, 2009, 27 (03) : 286 - 296
  • [3] Asymmetric synthesis of L-homophenylalanine by equilibrium-shift using recombinant aromatic L-amino acid transaminase
    Cho, BK
    Seo, JH
    Kang, TW
    Kim, BG
    BIOTECHNOLOGY AND BIOENGINEERING, 2003, 83 (02) : 226 - 234
  • [4] Optimized in vivo Synthesis of L-Homophenylalanine and L-Homotyrosine in E. coli
    Illies, Jan Hendrik
    PROTEIN SCIENCE, 2024, 33 : 165 - 165
  • [5] SpirOP, DPAMPP and asymmetric catalytic reaction
    Jiang, YZ
    Mi, AQ
    Deng, JG
    Gong, LZ
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2001, 21 (11) : 933 - 943
  • [6] Synthesis of L-homophenylalanine via integrated membrane bioreactor Influence of pH on yield
    Ahmad, A. L.
    Oh, P. C.
    Abd Shukor, S. R.
    BIOCHEMICAL ENGINEERING JOURNAL, 2010, 52 (2-3) : 296 - 300
  • [7] Asymmetrical synthesis of L-homophenylalanine using engineered Escherichia coli aspartate aminotransferase
    Lo, HH
    Hsu, SK
    Lin, WD
    Chan, NL
    Hsu, WH
    BIOTECHNOLOGY PROGRESS, 2005, 21 (02) : 411 - 415
  • [8] Practical synthesis of (-)-α-aminobenzolactam via nitration-cyclization of L-homophenylalanine ethyl ester
    Yu, Luoting
    Huang, Jiling
    Chang, Ching-Yao
    Yang, Teng-Kuei
    HETEROCYCLES, 2007, 71 (02) : 323 - 330
  • [9] Efficient Production of L-Homophenylalanine by Enzymatic-Chemical Cascade Catalysis
    Gao, Dengke
    Song, Wei
    Wu, Jing
    Guo, Liang
    Gao, Cong
    Liu, Jia
    Chen, Xiulai
    Liu, Liming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (36)
  • [10] Design phenylalanine dehydrogenase for L-homophenylalanine synthesis by conservation and co-evolution analysis
    Chen, Yuxin
    Zhang, Qian
    Lei, Hangbin
    Han, Yulong
    Wang, Shizhen
    CHEMICAL ENGINEERING SCIENCE, 2025, 304