Kinetic resolution of (±)-1-phenylethanol in [Bmim][PF6] using high activity preparations of lipases

被引：85
作者：
Shah, Shweta [1 ]
Gupta, Munishwar N. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 04期
关键词：
cross-linked enzyme aggregates; enantioselectivity; enzyme precipitated and rinsed with propanol; ionic liquids; lipases; propanol-rinsed enzyme preparation; protein coated microcrystals;
D O I：
10.1016/j.bmcl.2006.11.057
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Lipases from two different sources Candida rugosa (CRL) and Burkholderia cepacia (BCL) were formulated as enzyme precipitated and rinsed with organic solvents, organic solvent rinsed enzyme preparation, cross-linked enzyme aggregates (CLEAs) and protein coated micro-crystals (PCMCs). These various enzyme formulates were evaluated for the kinetic resolution of (+/-)-1-phenylethanol in ionic liquid [Bmim][PF6] by transesterification with vinyl acetate. Of all the enzyme forms evaluated EPRP and PCMC in the case of CRL showed the best results with 26% (E value = 153) and 53% (E value = 79) conversion, respectively, at 35 C in 24 h. Carrying out this conversion with PCMC at lower temperature of 25 C further improved the E value to 453 (with 44% conversion in 12 h). For BCL the acetone-rinsed enzyme preparation (AREP), CLEA and PCMC performed equally well with % conversion of 50 and 99 ee(P) (%) (E value > 1000) in just 2 h, whereas, the free lipase gave only 8% conversion. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：921 / 924
页数：4
相关论文
共 22 条
  • [1] Bornscheuer UT, 2000, METH TOOLS BIOSCI ME, P90
  • [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] Enhanced enantioselectivity of lipase from Pseudomonas sp at high temperatures and fixed water activity in the ionic liquid, 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]amide
    Eckstein, M
    Wasserscheid, P
    Kragl, U
    [J]. BIOTECHNOLOGY LETTERS, 2002, 24 (10) : 763 - 767
  • [4] Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: Reaction of enzyme anchored to the solvent
    Itoh, T
    Akasaki, E
    Kudo, K
    Shirakami, S
    [J]. CHEMISTRY LETTERS, 2001, (03) : 262 - 263
  • [5] A microwave-assisted microassay for lipases
    Jain, P
    Jain, S
    Gupta, MN
    [J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2005, 381 (07) : 1480 - 1482
  • [6] Biocatalysis in ionic liquids: Markedly enhanced enantioselectivity of lipase
    Kim, KW
    Song, B
    Choi, MY
    Kim, MJ
    [J]. ORGANIC LETTERS, 2001, 3 (10) : 1507 - 1509
  • [7] Enzyme-coated micro-crystals: a 1-step method for high activity biocatalyst preparation
    Kreiner, M
    Moore, BD
    Parker, MC
    [J]. CHEMICAL COMMUNICATIONS, 2001, (12) : 1096 - 1097
  • [8] Enzyme activation for nonaqueous media
    Lee, MY
    Dordick, JS
    [J]. CURRENT OPINION IN BIOTECHNOLOGY, 2002, 13 (04) : 376 - 384
  • [9] Cross-linked enzyme aggregates with enhanced activity:: application to lipases
    López-Serrano, P
    Cao, L
    van Rantwijk, F
    Sheldon, RA
    [J]. BIOTECHNOLOGY LETTERS, 2002, 24 (16) : 1379 - 1383
  • [10] Poly(ethylene glycol)-lipase complexes that are highly active and enantioselective in ionic liquids
    Maruyama, T
    Yamamura, H
    Kotani, T
    Kamiya, N
    Goto, M
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (08) : 1239 - 1244
123