IMPROVEMENT OF ENANTIOSELECTIVE ENZYMATIC ESTER HYDROLYSIS IN ORGANIC-SOLVENTS

被引:34
作者
RAKELS, JLL
STRAATHOF, AJJ
HEIJNEN, JJ
机构
[1] Department of Biochemical Engineering, 2628 BC Delft
关键词
D O I
10.1016/S0957-4166(00)80488-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A method is presented to improve the enzymatic enantioselective hydrolysis of chiral esters in water-saturated organic solvents. It is shown that addition of a non-reactive amine to the reaction mixture leads to the formation of an ion-pair with the produced carboxylic acid. Yield and enantiomeric excess are increased in lipase catalyzed kinetic resolutions of methyl 2-chloropropionate and glycidyl butyrate in various solvents. Chemical background hydrolysis was reduced with respect to aqueous solvents. A second phase was formed during reaction in apolar solvents, due to ion-pair formation, which may facilitate the isolation of the desired compound.
引用
收藏
页码:93 / 100
页数:8
相关论文
共 18 条
[1]  
AKITA H, 1989, CHEM PHARM BULL, V37, P2876
[2]  
ANDRADE MAC, 1991, BIOORG MED CHEM LETT, V7, P373
[3]   ENZYMATIC ACYLATION USING ACID ANHYDRIDES - CRUCIAL REMOVAL OF ACID [J].
BERGER, B ;
RABILLER, CG ;
KONIGSBERGER, K ;
FABER, K ;
GRIENGL, H .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :541-546
[4]   RESOLUTION OF SECONDARY ALCOHOLS USING LIPASE IN DIISOPROPYL ETHER [J].
BEVINAKATTI, HS ;
BANERJI, AA ;
NEWADKAR, RV .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2453-2455
[5]   SEQUENTIAL KINETIC RESOLUTION OF (+/-)-2,3-BUTANEDIOL IN ORGANIC-SOLVENT USING LIPASE FROM PSEUDOMONAS-CEPACIA [J].
CARON, G ;
KAZLAUSKAS, RJ .
TETRAHEDRON-ASYMMETRY, 1993, 4 (09) :1995-2000
[6]   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
[7]   ENZYMATIC-HYDROLYSIS OF 2,2,2,-TRIFLUOROETHYL ALPHA-CHLORO-ALPHA-PHENYLACETATE IN ORGANIC MEDIA [J].
GARCIA, MJ ;
BRIEVA, R ;
REBOLLEDO, F ;
GOTOR, V .
BIOTECHNOLOGY LETTERS, 1991, 13 (12) :867-870
[8]   UNUSUAL SOLVENT EFFECT ON PROTEASE ACTIVITY AND EFFECTIVE OPTICAL RESOLUTION OF AMINO-ACIDS BY HYDROLYTIC REACTIONS IN ORGANIC-SOLVENTS [J].
KISE, H ;
TOMIUCHI, Y .
BIOTECHNOLOGY LETTERS, 1991, 13 (05) :317-322
[9]   USE OF SALT HYDRATES TO BUFFER OPTIMAL WATER LEVEL DURING LIPASE CATALYZED SYNTHESIS IN ORGANIC MEDIA - A PRACTICAL PROCEDURE FOR ORGANIC CHEMISTS [J].
KVITTINGEN, L ;
SJURSNES, B ;
ANTHONSEN, T ;
HALLING, P .
TETRAHEDRON, 1992, 48 (13) :2793-2802
[10]   LIPASE-CATALYZED ASYMMETRIC HYDROLYSIS OF 3-PHENYLGLYCIDIC ACID ESTER, THE KEY INTERMEDIATE IN THE SYNTHESIS OF DILTIAZEM HYDROCHLORIDE [J].
MATSUMAE, H ;
FURUI, M ;
SHIBATANI, T .
JOURNAL OF FERMENTATION AND BIOENGINEERING, 1993, 75 (02) :93-98