Enantioselectivity of alcohol-treated Candida rugosa lipase in the kinetic resolution of racemic methyl 2-aryloxypropionates in water and aqueous organic media

被引：18

作者：

Cipiciani, A ^{[1
]}

Bellezza, F ^{[1
]}

Fringuelli, F ^{[1
]}

Stillitano, M ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim, I-06100 Perugia, Italy

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(99)00500-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Racemic methyl 2-aryloxypropionates (+/-)-1 were subjected to hydrolysis in water and in a series of two-phase aqueous organic media in the presence of Candida rugosa lipase (CRL). The biocatalytic material used was the enzyme of commercial CRL purified by treatment with different alcohols. The purification of CRL and the reaction medium play an important role in the enantioselection of racemates (+/-)-1 While it is not possible to use the same protocol for all substrates, by combining the different ways of purifying the enzyme with the various reaction media, it is possible to achieve high enantioselectivities of racemic esters. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4599 / 4605

页数：7

共 21 条

[1] THE ESTERASE PROFILE OF A LIPASE FROM CANDIDA-CYLINDRACEA [J].

BRAHIMIHORN, MC ;

GUGLIELMINO, ML ;

ELLING, L ;

SPARROW, LG .

BIOCHIMICA ET BIOPHYSICA ACTA, 1990, 1042 (01) :51-54

[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTION OF ENANTIOMERS .2. ENZYME-CATALYZED ESTERIFICATIONS IN WATER ORGANIC-SOLVENT BIPHASIC SYSTEMS [J].

CHEN, CS ;

WU, SH ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2812-2817

[3] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[4] Enzymatic kinetic resolution of (+/-)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase. An efficient route for the preparation of (+)-R-4-hydroxy- and (+)-S-4-acetoxy[2.2]paracyclophane [J].

Cipiciani, A ;

Fringuelli, F ;

Mancini, V ;

Piermatti, O ;

Scappini, AM ;

Ruzziconi, R .

TETRAHEDRON, 1997, 53 (34) :11853-11858

[5] Improving the enantioselectivity of Candida rugosa lipase in the kinetic resolution of racemic methyl 2-(2,4-dichlorophenoxy)propionate [J].

Cipiciani, A ;

Cittadini, M ;

Fringuelli, F .

TETRAHEDRON, 1998, 54 (27) :7883-7890

[6] A 2-PROPANOL TREATMENT INCREASES THE ENANTIOSELECTIVITY OF CANDIDA-RUGOSA LIPASE TOWARD ESTERS OF CHIRAL CARBOXYLIC-ACIDS [J].

COLTON, IJ ;

AHMED, SN ;

KAZLAUSKAS, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :212-217

[7] ENANTIOMERS OF CLOFIBRIC ACID ANALOGS HAVE OPPOSITE ACTIONS ON RAT SKELETAL-MUSCLE CHLORIDE CHANNELS [J].

CONTECAMERINO, D ;

MAMBRINI, M ;

DELUCA, A ;

TRICARICO, D ;

BRYANT, SH ;

TORTORELLA, V ;

BETTONI, G .

PFLUGERS ARCHIV-EUROPEAN JOURNAL OF PHYSIOLOGY, 1988, 413 (01) :105-107

[8]

FREDGA A, 1961, ARK KEMI, V17, P265

[9]

GROCHULSKI P, 1993, J BIOL CHEM, V268, P12843

[10]

HERNAIZ MJ, 1994, TETRAHEDRON, V50, P10749

← 1 2 3 →