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
  • [1] Use of lipases for the kinetic resolution of lactic acid esters in heptane or in a solvent free system
    Richard, Gaetan
    Nott, Katherine
    Nicks, Francois
    Paquot, Michel
    Blecker, Christophe
    Fauconnier, Marie-Laure
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 97 : 289 - 296
  • [2] Dynamic kinetic resolution of α-amino acid esters in the presence of aldehydes
    Schichl, Daniel A.
    Enthaler, Stephan
    Holla, Wolfgang
    Riermeier, Thomas
    Kragl, Udo
    Beller, Matthias
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (20) : 3506 - 3512
  • [3] Kinetic resolution of amine-alcohols and esters by insolubilized microbial lipases
    Ortiz Lopez, Claudia
    Barbosa, Oveimar
    Escorcia, Andres
    Dellamora-Ortiz, Gisela
    Torres, Rodrigo
    JOURNAL OF BIOTECHNOLOGY, 2008, 136 : S346 - S347
  • [4] Asymmetric synthesis of silylated α-amino acid esters through dynamic kinetic resolution
    Chen, JX
    Tunge, JA
    Norton, JR
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12): : 4366 - 4369
  • [5] Lipase/ruthenium-catalyzed dynamic kinetic resolution of tropic acid ethyl esters
    Atuu, MR
    Hossain, MM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U30 - U30
  • [6] Ammonolysis of carboxylic esters catalyzed by lipases - Synthesis of fatty acid amides
    De Zoete, MC
    Kock-Van Dalen, AC
    Van Rantwijk, F
    Sheldon, RA
    ENZYME ENGINEERING XIII, 1996, 799 : 346 - 350
  • [7] Enantioselective hydrolysis of amino acid esters by apomyoglobin: perfect kinetic resolution of a phenylalanine derivative
    Tomisaka, K
    Ishida, Y
    Konishi, K
    Aida, T
    CHEMICAL COMMUNICATIONS, 2001, (01) : 133 - 134
  • [8] KINETIC RESOLUTION OF N-PROTECTED AMINO-ACID ESTERS IN ORGANIC-SOLVENTS CATALYZED BY A STABLE INDUSTRIAL ALKALINE PROTEASE
    CHEN, ST
    CHEN, SY
    HSIAO, SC
    WANG, KT
    BIOTECHNOLOGY LETTERS, 1991, 13 (11) : 773 - 778
  • [9] Dynamic kinetic resolution of α-hydroxy acid esters
    Huerta, FF
    Laxmi, YRS
    Bäckvall, JE
    ORGANIC LETTERS, 2000, 2 (08) : 1037 - 1040
  • [10] Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
    Alatorre-Santamaria, Sergio
    Rodriguez-Mata, Maria
    Gotor-Fernandez, Vicente
    de Mattos, Marcos Carlos
    Sayago, Francisco J.
    Jimenez, Ana I.
    Cativiela, Carlos
    Gotor, Vicente
    TETRAHEDRON-ASYMMETRY, 2008, 19 (14) : 1714 - 1719