A 2-PROPANOL TREATMENT INCREASES THE ENANTIOSELECTIVITY OF CANDIDA-RUGOSA LIPASE TOWARD ESTERS OF CHIRAL CARBOXYLIC-ACIDS

被引:148
作者
COLTON, IJ [1 ]
AHMED, SN [1 ]
KAZLAUSKAS, RJ [1 ]
机构
[1] MCGILL UNIV, DEPT CHEM, MONTREAL, PQ H3A 2K6, CANADA
关键词
D O I
10.1021/jo00106a036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Crude lipase from Candida rugosa (CRL) is a poorly to moderately enantioselective catalyst for the hydrolysis of esters of 2-substituted carboxylic acids such as 2-arylpropanoic acids (E = 4-10) and 2-(aryloxy)propanoic acids (E = 2-17). Previous workers converted CRL into a high enantioselectivity form using a four-step purification procedure that included an organic solvent treatment. In this paper we report a simple 2-propanol treatment that converts crude CRL to the high enantioselectivity form. Dissolving crude commercial CRL in 50% 2-propanol followed by dialysis to remove 2-propanol increased the total activity by a factor of 1.2-1.6 and the enantioselectivity toward seven carboxylic acids by a factor of 2.3 to >25. We demonstrated synthetic use of this 2-propanol-treated CRL by resolving 10 g of methyl 2-(4-chlorophenoxy)propionate (3-methyl ester), yielding 2.8 g of product acid (93.1% ee R, a serum cholesterol-lowering compound) and 4.7 g of recovered ester (94.4% ee S), corresponding to an enantiomeric ratio of 100 for the resolution. Recent X-ray crystal structures identified two conformational forms of CRL-open and closed. We suggest that the 2-propanol treatment may increase the activity and enantioselectivity by converting the closed form of CRL to the open form.
引用
收藏
页码:212 / 217
页数:6
相关论文
共 53 条
  • [31] RESOLUTION OF RACEMIC CARBOXYLIC-ACIDS VIA THE LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING VINYL ESTERS - EFFECTS OF ALCOHOLS AS NUCLEOPHILES AND ORGANIC-SOLVENTS ON ENANTIOSELECTIVITY
    MIYAZAWA, T
    KURITA, S
    UEJI, S
    YAMADA, T
    KUWATA, S
    [J]. BIOTECHNOLOGY LETTERS, 1992, 14 (10) : 941 - 946
  • [32] MUTSAERS JHGM, 1991, RECL TRAV CHIM PAY B, V110, P185
  • [33] NG YC, 1994, J ORG CHEM, V59, P2075
  • [34] CHROMATOGRAPHIC RESOLUTION .19. DIRECT OPTICAL RESOLUTION OF CARBOXYLIC-ACIDS BY CHIRAL HPLC ON TRIS(3,5-DIMETHYLPHENYLCARBAMATE)S OF CELLULOSE AND AMYLOSE
    OKAMOTO, Y
    ABURATANI, R
    KAIDA, Y
    HATADA, K
    [J]. CHEMISTRY LETTERS, 1988, (07) : 1125 - 1128
  • [35] DIRECT CHROMATOGRAPHIC-SEPARATION OF 2-ARYLPROPIONIC ACID ENANTIOMERS USING TRIS(3,5-DIMETHYLPHENYLCARBAMATE)S OF CELLULOSE AND AMYLOSE AS CHIRAL STATIONARY PHASES
    OKAMOTO, Y
    ABURATANI, R
    KAIDA, Y
    HATADA, K
    INOTSUME, N
    NAKANO, M
    [J]. CHIRALITY, 1989, 1 (03) : 239 - 242
  • [36] CIS-TRANSISOMERIZATION AT PROLINE - DESOLVATION AND ITS CONSEQUENCES FOR PROTEIN FOLDING
    RADZICKA, A
    ACHESON, SA
    WOLFENDEN, R
    [J]. BIOORGANIC CHEMISTRY, 1992, 20 (04) : 382 - 386
  • [37] LIPASE-CATALYZED KINETIC RESOLUTION OF RACEMIC (+/-)2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)-CYCLOPROPANE CARBOXYL ESTERS
    RAO, AB
    REHMAN, H
    KRISHNAKUMARI, B
    YADAV, JS
    [J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2611 - 2614
  • [38] PURIFICATION AND CHARACTERIZATION OF 2 DISTINCT LIPASES FROM CANDIDA-CYLINDRACEA
    RUA, ML
    DIAZMAURINO, T
    FERNANDEZ, VM
    OTERO, C
    BALLESTEROS, A
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA, 1993, 1156 (02) : 181 - 189
  • [39] RUBIN B, 1991, GBF MONOG SERIES, P63
  • [40] SECOR J, 1989, BIOCATALYSIS AGR BIO, P265