Remarkable enhancement of lipase catalytic activity: Combined effects of acyl donor and thiacrown ether additive during trans-esterification of 5-phenyl-1-penten-3-ol

被引:20
作者
Takagi, Y [1 ]
Ino, R
Kihara, H
Itoh, T
Tsukube, H
机构
[1] Hyogo Univ Teacher Educ, Dept Nat Sci, Yashiro, Hyogo 67314, Japan
[2] Okayama Univ, Fac Educ, Dept Chem, Okayama 700, Japan
[3] Osaka City Univ, Fac Sci, Dept Chem, Osaka 558, Japan
关键词
D O I
10.1246/cl.1997.1247
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Pseudomonas cepacia lipase-catalyzed transesterification of 5-phenyl-1-penten-3-ol was drastically accelerated by 5 mol% of a thiacrown ether additive. The reaction profile was strongly dependent on the nature of the vinyl esters as the acyl donor; the highest acceleration rate was recorded with vinyl chloroacetate, while the highest enantioselectivity was obtained using vinyl acetate.
引用
收藏
页码:1247 / 1248
页数:2
相关论文
共 10 条
  • [1] 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
  • [2] Significant effect of acyl groups on enantioselectivity in lipase-catalyzed transesterifications
    Ema, T
    Maeno, S
    Takaya, Y
    Sakai, T
    Utaka, M
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (03) : 625 - 628
  • [3] Effects of crown ethers and small amounts of cosolvent on the activity and enantioselectivity of alpha-chymotrypsin in organic solvents
    Engbersen, JFJ
    Broos, J
    Verboom, W
    Reinhoudt, DN
    [J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (11) : 2171 - 2178
  • [4] Crown ethers as regulators of enzymatic reactions: Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis of 2-cyano-1-methylethyl acetate
    Itoh, T
    Takagi, Y
    Murakami, T
    Hiyama, Y
    Tsukube, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) : 2158 - 2163
  • [5] Itoh T, 1997, TREND ORGAN CHEM, V6, P1
  • [6] ITOH T, 1996, PREPARATIVE BIOTRANS
  • [7] RESOLUTION OF MANDELIC-ACIDS BY LIPASE-CATALYZED TRANSESTERIFICATIONS IN ORGANIC MEDIA - INVERSION OF ENANTIOSELECTIVITY MEDIATED BY THE ACYL DONOR
    MIYAZAWA, T
    KURITA, S
    UEJI, S
    YAMADA, T
    KUWATA, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18): : 2253 - 2255
  • [8] THE EFFECT OF CROWN ETHERS ON ENZYME-CATALYZED REACTIONS IN ORGANIC-SOLVENTS
    REINHOUDT, DN
    EENDEBAK, AM
    NIJENHUIS, WF
    VERBOOM, W
    KLOOSTERMAN, M
    SCHOEMAKER, HE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) : 399 - 400
  • [9] Thiacrown ether as regulator of lipase-catalyzed trans-esterification in organic media: Practical optical resolution of allyl alcohols
    Takagi, Y
    Teramoto, J
    Kihara, H
    Itoh, T
    Tsukube, H
    [J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4991 - 4992
  • [10] WONG CH, 1994, ENZYMES SYNTHETIC OR