Control of enantioselectivity of lipase-catalyzed esterification in supercritical carbon dioxide by tuning the pressure and temperature

被引:41
作者
Matsuda, T [1 ]
Kanamaru, R
Watanabe, K
Kamitanaka, T
Harada, T
Nakamura, K
机构
[1] Ryukoku Univ, Fac Sci & Technol, Dept Chem Mat, Otsu, Shiga 5202194, Japan
[2] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan
关键词
D O I
10.1016/S0957-4166(03)00431-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The enantioselectivity of lipase-catalyzed esterification of 1-(p-chlorophenyl)-2,2,2-trifluoroethanol in supercritical carbon dioxide was controlled by tuning the pressure and temperature. The enantioselectivity was higher at low pressure and low temperature (E=60) than at high pressure and high temperature (E=10). At the density of 0.75 g/mL, a modified Eyring plot of In E against 1/T was found to be linear, as expected from the theory on the effects of temperature on stereochemistry. (C) 2003 Published by Elsevier Science Ltd.
引用
收藏
页码:2087 / 2091
页数:5
相关论文
共 28 条
  • [1] Control of subtilisin substrate specificity by solvent engineering in organic solvents and supercritical fluoroform
    Chaudhary, AK
    Kamat, SV
    Beckman, EJ
    Nurok, D
    Kleyle, RM
    Hajdu, P
    Russell, AJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) : 12891 - 12901
  • [2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [3] Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media
    Hamada, H
    Shiromoto, M
    Funahashi, M
    Itoh, T
    Nakamura, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) : 2332 - 2336
  • [4] AN ACCURATE EQUATION OF STATE FOR CARBON-DIOXIDE
    HUANG, FH
    LI, MH
    LEE, LL
    STARLING, KE
    CHUNG, FTH
    [J]. JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, 1985, 18 (06) : 490 - 496
  • [5] SOLVENT EFFECTS ON AN ENZYMATIC ESTER SYNTHESIS IN SUPERCRITICAL CARBON-DIOXIDE
    IKUSHIMA, Y
    SAITO, N
    YOKOYAMA, T
    HATAKEDA, K
    ITO, S
    ARAI, M
    BLANCH, HW
    [J]. CHEMISTRY LETTERS, 1993, (01) : 109 - 112
  • [6] ACTIVATION OF A LIPASE TRIGGERED BY INTERACTIONS WITH SUPERCRITICAL CARBON-DIOXIDE IN THE NEAR-CRITICAL REGION
    IKUSHIMA, Y
    SAITO, N
    ARAI, M
    BLANCH, HW
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (22) : 8941 - 8944
  • [7] Ikushima Y, 1997, ADV COLLOID INTERFAC, V71-2, P259
  • [8] Systematic synthesis of multifluorinated α,α-difluoro-γ-lactones through intramolecular radical cyclization
    Itoh, T
    Sakabe, K
    Kudo, K
    Ohara, H
    Takagi, Y
    Kihara, H
    Zagatti, P
    Renou, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 252 - 265
  • [9] Homogeneous catalysis in supercritical fluids
    Jessop, PG
    Ikariya, T
    Noyori, R
    [J]. CHEMICAL REVIEWS, 1999, 99 (02) : 475 - 493
  • [10] Iridium-catalyzed enantioselective hydrogenation of imines in supercritical carbon dioxide
    Kainz, S
    Brinkmann, A
    Leitner, W
    Pfaltz, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) : 6421 - 6429