Enantiomer selective acylation of racemic alcohols by lipases in continuous-flow bioreactors

被引：86

作者：

Csajagi, Csaba ^{[1
]}

Szatzker, Gabor ^{[2
,3
]}

Toke, Eniko Rita ^{[2
,3
]}

Uerge, Laszlo ^{[1
]}

Darvas, Ferenc ^{[1
]}

Poppe, Laszlo ^{[2
,3
]}

机构：

[1] ThalesNano Nanotechnol Inc, Graphisoft Pk, H-1031 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Hungarian Acad Sci, Dept Organ Chem & Technol, H-1111 Budapest, Hungary

[3] Budapest Univ Technol & Econ, Hungarian Acad Sci, Res Grp Alkaloid Chem, H-1111 Budapest, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 02期

基金：

匈牙利科学研究基金会;

关键词：

D O I：

10.1016/j.tetasy.2008.01.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Continuous-flow mode enantiomer selective acetylations of racemic 1-phenylethanol, 1-cyclohexylethanol, and 1-phenylpropan-2-ol (rac-1a-c, respectively) with vinyl acetate were performed in small stainless steel packed-bed reactors filled with different commercial lipase preparations. In several lipase-filled columns, highly enantiomer selective (E> 100) kinetic resolutions of these alcohols were achieved. In most cases, comparison of the continuous-flow and batch mode (shake flask) biotransformations indicated similar enantiomer selectivities (E) but higher productivities (specific reaction rate: r) in the corresponding continuous-flow reaction. The effect of temperature (0-60 degrees C) and pressure (1-120 bar) on the continuous-flow acetylation of racemic 1-phenylpropan-2-ol was investigated in an immobilized Candida antarctica lipase B (CaLB) filled reactor. Pressure had no significant effect on r and E. Expectedly, a monotonous increase of specific reaction rate (r) was observed within this temperature range. Most surprisingly, the enantiomer selectivity had a maximum (E similar to 25, at 20 degrees C) and a minimum (E similar to 7, at 50 degrees C). The continuous-flow reactions in CaLB-filled columns were successfully applied for preparative scale kinetic resolutions of rac-1a-c. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：237 / +

页数：12

共 54 条

[1] Production of biodiesel by lipase-catalyzed transesterification of vegetable oils: A kinetics study
Al-Zuhair, S
[J]. BIOTECHNOLOGY PROGRESS, 2005, 21 (05) : 1442 - 1448
[2] Arcos JA, 2000, BIOTECHNOL BIOENG, V68, P563, DOI 10.1002/(SICI)1097-0290(20000605)68:5<563::AID-BIT11>3.0.CO
[3] 2-H
[4] ENZYMATIC RESOLUTION OF (S)-(+)-NAPROXEN IN A CONTINUOUS REACTOR
BATTISTEL, E
BIANCHI, D
CESTI, P
PINA, C
[J]. BIOTECHNOLOGY AND BIOENGINEERING, 1991, 38 (06) : 659 - 664
[5] Non-isothermal lipase-catalyzed kinetic resolution in a packed bed reactor: Modeling, simulation and miniplant studies
Berendsen, W. R.
Lapin, A.
Reuss, M.
[J]. CHEMICAL ENGINEERING SCIENCE, 2007, 62 (09) : 2375 - 2385
[6] ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS
BIANCHI, D
CESTI, P
BATTISTEL, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) : 5531 - 5534
[7] Novel hydrolases from thermophilic filamentous fungi for enantiomerically and enantiotopically selective Biotransformations
Bódai, V
Peredi, R
Bálint, J
Egri, G
Novák, L
Szakacs, G
Poppe, L
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (6-7) : 811 - 818
[8] Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
[9] 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
[10] Enantioselective synthesis of (S)-ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on accurel MP1000
Chen, JC
Tsai, SW
[J]. BIOTECHNOLOGY PROGRESS, 2000, 16 (06) : 986 - 992

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