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
  • [11] CONTROL OF ENZYME ENANTIOSELECTIVITY WITH PRESSURE CHANGES IN SUPERCRITICAL FLUOROFORM
    KAMAT, SV
    BECKMAN, EJ
    RUSSELL, AJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) : 8845 - 8846
  • [12] Kiran E., 2000, SUPERCRITICAL FLUIDS
  • [13] KITAZUME T, 1991, ACS SYM SER, V456, P175
  • [14] Two classes of enzymes of opposite stereochemistry in an organism: One for fluorinated and another for nonfluorinated substrates
    Matsuda, T
    Harada, T
    Nakajima, N
    Itoh, T
    Nakamura, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) : 157 - 163
  • [15] Control on enantioselectivity with pressure for lipase-catalyzed esterification in supercritical carbon dioxide
    Matsuda, T
    Kanamaru, R
    Watanabe, K
    Harada, T
    Nakamura, K
    [J]. TETRAHEDRON LETTERS, 2001, 42 (47) : 8319 - 8321
  • [16] Supercritical biocatalysis
    Mesiano, AJ
    Beckman, EJ
    Russell, AJ
    [J]. CHEMICAL REVIEWS, 1999, 99 (02) : 623 - 633
  • [17] Reversible control of enzymatic transglycosylations in supercritical fluoroform using a lipid-coated β-D-galactosidase
    Mori, T
    Li, M
    Kobayashi, A
    Okahata, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1188 - 1189
  • [18] Reversible activity changes of a lipid-coated lipase for enantioselective esterification in supercritical fluoroform
    Mori, T
    Funasaki, M
    Kobayashi, A
    Okahata, Y
    [J]. CHEMICAL COMMUNICATIONS, 2001, (18) : 1832 - 1833
  • [19] STATIC RELATIVE PERMITTIVITY OF CARBON-DIOXIDE AND NITROUS-OXIDE UP TO 30-MPA
    MORIYOSHI, T
    KITA, T
    UOSAKI, Y
    [J]. BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1993, 97 (04): : 589 - 596
  • [20] ADSORPTION OF CARBON-DIOXIDE ON PROTEINS IN THE SUPERCRITICAL REGION
    NAKAMURA, K
    HOSHINO, T
    ARIYAMA, H
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (09): : 2341 - 2347