Kinetic resolution of amino acid esters catalyzed by lipases

被引:0
|
作者
Houng, JY [1 ]
Wu, ML [1 ]
Chen, ST [1 ]
机构
[1] ACAD SINICA,INST BIOL CHEM,TAIPEI,TAIWAN
关键词
lipase; resolution; amino acids; unnatural amino acids; enantioselectivity;
D O I
10.1002/(SICI)1520-636X(1996)8:6<418::AID-CHIR2>3.0.CO;2-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Racemic amino acids were resolved by lipase via hydrolysis of their esters. Lipases (Pseudomonas lipase from Amano PS, Rhizopus lipase from Serva, and porcine pancrease lipase from Sigma) could selectively hydrolyze the L-amino acid esters in aqueous solution with high reactivities and selectivities. The effect of the structural changes in the ester moiety on the stereoselectivity of the lipases was also investigated using D,L-homophenylalanine as a model. Procedures were developed for the resolution of natural and unnatural amino acids. (C) 1996 Wiley-Liss, Inc.
引用
收藏
页码:418 / 422
页数:5
相关论文
共 50 条
  • [41] L-Lactate-mediated Dynamic Kinetic Resolution of α-Bromo Esters for Asymmetric Syntheses of α-Amino Acid Derivatives
    Kim, Yelim
    Park, Kon Ji
    Choi, Yun Soo
    Lee, Myung-su
    Park, Yong Sun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (08): : 2531 - 2534
  • [42] Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters
    Yu, Kunru
    Liu, Xiaohua
    Lin, Xiaobin
    Lin, Lili
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2015, 51 (80) : 14897 - 14900
  • [43] Kinetic Resolution of Aliphatic β-Amino Acid Amides by β-Aminopeptidases
    Heck, Tobias
    Seebach, Dieter
    Osswald, Steffen
    ter Wiel, Matthijs K. J.
    Kohler, Hans-Peter E.
    Geueke, Birgit
    CHEMBIOCHEM, 2009, 10 (09) : 1558 - 1561
  • [44] Kinetic Resolution of 2-Methylbutyric Acid and Its Ester by Esterification and Hydrolysis with Lipases
    Li Xiaolu
    Wang Dong
    Xu Yan
    Geng Yawei
    Chen Cong
    Wang Nan
    CHINESE JOURNAL OF CATALYSIS, 2009, 30 (09) : 951 - 957
  • [45] Dynamic kinetic resolution:: an efficient route to anti α-amino-β-hydroxy esters via Ru-SYNPHOS® catalyzed hydrogenation
    Mordant, C
    Dünkelmann, P
    Ratovelomanana-Vidal, V
    Genet, JP
    CHEMICAL COMMUNICATIONS, 2004, (11) : 1296 - 1297
  • [46] Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
    Yang, Hui
    Zheng, Wen-Hua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (45) : 16177 - 16180
  • [47] Ethyl acetate as an acyl donor in the continuous flow kinetic resolution of (±)-1-phenylethylamine catalyzed by lipases
    de Miranda, Amanda S.
    Miranda, Leandro S. M.
    de Souza, Rodrigo O. M. A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (20) : 3332 - 3336
  • [48] Kinetic properties of Penicillium cyclopium lipases studied with vinyl esters
    Chahinian, H
    Nini, L
    Boitard, E
    Dubès, JP
    Sarda, L
    Comeau, LC
    LIPIDS, 2000, 35 (08) : 919 - 925
  • [49] In depth analysis of heterogeneous catalysts for the chemoenzymatic dynamic kinetic resolution of β-amino esters
    Adriaensen, Koen
    Vercammen, Jannick
    Van Goethem, Cedric
    Agrawal, Kumar Varoon
    De Vos, Dirk
    CATALYSIS SCIENCE & TECHNOLOGY, 2022, 12 (09) : 2894 - 2902
  • [50] Synthesis of Chiral Benzimidazoles as Acylating Agents for Kinetic Resolution of Racemic α-Amino Esters
    Xu, Hao
    Tian, Hua
    Zheng, Liangyu
    Liu, Qingwen
    Wang, Li
    Zhang, Suoqin
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (05) : 1108 - 1113