DIFFERENT ENANTIOSELECTIVITY AND REGIOSELECTIVITY OF THE CYTOSOLIC AND MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF SIMPLE PHENYL-SUBSTITUTED EPOXIDES

被引：35

作者：

BELLUCCI, G

CHIAPPE, C

CORDONI, A

MARIONI, F

机构：

[1] Dipartimento di Chimica Bioorganica, 56126 Pisa

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(00)73156-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cytosolic (cEH) and the microsomal epoxide hydrolase (mEH) hydrolyse styrene oxide and trans-1-phenylpropene oxide with different enantioselectivity and regioselectivity. While mEH always leads to a regiospecific and enantioselective opening at the non-benzylic oxirane carbon, cEH gives a non-regioselective and non-enantioselective attack to styrene oxide and a regiospecific and non-enantioselective snack at the benzylic carbon of 1-phenylpropene oxide.

引用

收藏

页码：4219 / 4222

页数：4

相关论文

共 21 条

[1] ENZYME-CATALYZED DETOXICATION REACTIONS - MECHANISMS AND STEREOCHEMISTRY [J].

ARMSTRONG, RN .

CRC CRITICAL REVIEWS IN BIOCHEMISTRY, 1987, 22 (01) :39-88

[2] SUBSTRATE ENANTIOSELECTIVITY IN THE RABBIT LIVER MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF TRANS AND CIS 1-PHENYLPROPENE OXIDES - A COMPARISON WITH STYRENE OXIDE [J].

BELLUCCI, G ;

CHIAPPE, C ;

CORDONI, A ;

MARIONI, F .

TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1153-1160

[3] SUBSTRATE ENANTIOSELECTION IN THE MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF MONOSUBSTITUTED OXIRANES - EFFECTS OF BRANCHING OF ALKYL CHAINS [J].

BELLUCCI, G ;

CHIAPPE, C ;

CONTI, L ;

MARIONI, F ;

PIERINI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5978-5983

[4] ENANTIOSELECTIVITY OF THE ENZYMATIC-HYDROLYSIS OF CYCLOHEXENE OXIDE AND (+/-)-1-METHYLCYCLOHEXENE OXIDE - A COMPARISON BETWEEN MICROSOMAL AND CYTOSOLIC EPOXIDE HYDROLASES [J].

BELLUCCI, G ;

CHIAPPE, C ;

MARIONI, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2369-2373

[5] PRODUCT ENANTIOSELECTIVITY OF THE MICROSOMAL AND CYTOSOLIC EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF MESO EPOXIDES [J].

BELLUCCI, G ;

CAPITANI, I ;

CHIAPPE, C ;

MARIONI, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) :1170-1171

[6] REGIOSELECTIVITY AND ENANTIOSELECTIVITY OF THE CYTOSOLIC EPOXIDE HYDROLASE-CATALYZED HYDROLYSIS OF RACEMIC MONOSUBSTITUTED ALKYLOXIRANES [J].

BELLUCCI, G ;

CHIAPPE, C ;

MARIONI, F ;

BENETTI, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :361-363

[7]

BELLUCCI G, 1992, INDIAN J CHEM B, V31, P828

[8]

BELLUCCI G, 1981, BIOCHEM BIOPH RES CO, V103, P838

[9]

DEMONTELLANO PRO, 1986, CYTOCHROME P450 STRU, P217

[10] THE INTERACTION OF CYTOSOLIC EPOXIDE HYDROLASE WITH CHIRAL EPOXIDES [J].

DIETZE, EC ;

KUWANO, E ;

HAMMOCK, BD .

INTERNATIONAL JOURNAL OF BIOCHEMISTRY, 1993, 25 (01) :43-52