A drop of enantioselectivity in the Pseudomonas cepacia lipase-catalyzed ester hydrolysis is influenced by the chain length of the fatty acid

被引:7
|
作者
Tafi, A
Manetti, F
Botta, M
Casati, S
Santaniello, E
机构
[1] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy
[2] Univ Milan, Dipartimento Sci Preclin LITA Vialba, I-20157 Milan, Italy
关键词
D O I
10.1016/j.tetasy.2004.06.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A two-step molecular mechanics based computational procedure has been applied to explain the enantioselectivity observed in the hydrolysis of esters of primary alcohols, carried out in the presence of a lipase from Pseudomonas cepacia. This approach proved to be very effective in explaining an unpredictable drop in enantioselectivity, experimentally observed when the chain of the fatty acid was lengthened and to predict the chain length in correspondence of which the effect should have revealed itself. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2345 / 2350
页数:6
相关论文
共 50 条
  • [1] Improvement of the enantioselectivity of lipase-catalyzed naproxen ester hydrolysis in organic solvent
    Xin, JY
    Li, SB
    Chen, XH
    Wang, LL
    Xu, Y
    [J]. ENZYME AND MICROBIAL TECHNOLOGY, 2000, 26 (2-4) : 137 - 141
  • [2] Factors influencing enantioselectivity of lipase-catalyzed hydrolysis
    Kinoshita, M
    Ohno, A
    [J]. TETRAHEDRON, 1996, 52 (15) : 5397 - 5406
  • [3] ENANTIOSELECTIVE LIPASE-CATALYZED ESTER HYDROLYSIS - EFFECTS ON RATES AND ENANTIOSELECTIVITY FROM A VARIATION OF THE ESTER STRUCTURE
    BOJARSKI, J
    OXELBARK, J
    ANDERSSON, C
    ALLENMARK, S
    [J]. CHIRALITY, 1993, 5 (03) : 154 - 158
  • [4] Benzyl ester amidations catalyzed by Pseudomonas cepacia lipase
    Grote, J
    Adamczyk, M
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 515 - ORGN
  • [5] Enzyme recycling does not influence the enantioselectivity of the Pseudomonas cepacia lipase-catalyzed acylation of a racemic alcohol in organic solvents
    Casati, S
    Caporali, M
    Ferraboschi, P
    Manzocchi, A
    Santaniello, E
    [J]. BIOTECHNOLOGY TECHNIQUES, 1997, 11 (02) : 81 - 83
  • [6] Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids
    Ganske, F
    Bornscheuer, UT
    [J]. ORGANIC LETTERS, 2005, 7 (14) : 3097 - 3098
  • [7] Lipase-Catalyzed Synthesis of Fatty Acid Pyridylcarbinol Ester for the Analysis of Seed Lipids
    Kim, Chang-Su
    Lim, Do-Hyung
    Keum, Young Soo
    [J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2016, 93 (03) : 339 - 346
  • [8] Computer simulations of enantioselective ester hydrolyses catalyzed by Pseudomonas cepacia lipase
    Tafi, A
    van Almsick, A
    Corelli, F
    Crusco, M
    Laumen, KE
    Schneider, MP
    Botta, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3659 - 3665
  • [9] LIPASE-CATALYZED HYDROLYSIS OF CROWNED ESTER SUBSTRATES - METAL CATION-ENHANCED REACTIVITY AND ENANTIOSELECTIVITY OF 12-CROWN-4 ESTER
    TSUKUBE, H
    BETCHAKU, A
    HIYAMA, Y
    ITOH, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23): : 7014 - 7018
  • [10] Lipase-catalyzed synthesis of fatty acid diethanolamides
    Liu, KJ
    Nag, A
    Shaw, JF
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (12) : 5761 - 5764