KINETIC RESOLUTION BY EPOXIDE HYDROLASE CATALYZED HYDROLYSIS OF RACEMIC METHYL-SUBSTITUTED METHYLENECYCLOHEXENE OXIDES

被引：15

作者：

BELLUCCI, G

CHIAPPE, C

INGROSSO, G

ROSINI, C

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56126 PISA,ITALY

[2] UNIV LECCE,DIPARTIMENTO BIOL,I-73100 LECCE,ITALY

[3] CNR,CSMSOA,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00250-S

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A complete kinetic resolution of 2,2-dimethylmethylenecyclobexene oxide and a partial resolution of the cis and trans-2-methylmethylenecyclohexene oxides, but not of their 3-methyl substituted isomers, have been achieved by partial hydrolysis to the corresponding diols using the microsomal epoxide hydrolase. No substrate enantioselectivity was in found for the hydrolysis of all these substrates by the cytosolic epoxide hydrolase.

引用

页码：1911 / 1918

页数：8

共 24 条

[1] AN EXTENSION OF THE QUADRANT RULE IN OXIRANES TO NONALKYL SUBSTITUENTS - THE CD OF R(-)-EPICHLOROHYDRIN AND S(+)-EPICHLOROHYDRIN
BASIL, A
BENTZUR, S
GEDANKEN, A
RODGER, A
[J]. CHEMICAL PHYSICS LETTERS, 1991, 180 (05) : 482 - 484
[2] ENANTIOSELECTIVITY OF THE MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF TRANS-4,5-DIMETHYL-1,2-EPOXYCYCLOHEXANE
BELLUCCI, G
BERTI, G
FERRETTI, M
MASTRORILLI, E
SILVESTRI, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1471 - 1474
[3] SUBSTRATE ENANTIOSELECTIVITY IN THE RABBIT LIVER MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF TRANS AND CIS 1-PHENYLPROPENE OXIDES - A COMPARISON WITH STYRENE OXIDE
BELLUCCI, G
CHIAPPE, C
CORDONI, A
MARIONI, F
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (06) : 1153 - 1160
[4] DIFFERENT ENANTIOSELECTIVITY AND REGIOSELECTIVITY OF THE CYTOSOLIC AND MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF SIMPLE PHENYL-SUBSTITUTED EPOXIDES
BELLUCCI, G
CHIAPPE, C
CORDONI, A
MARIONI, F
[J]. TETRAHEDRON LETTERS, 1994, 35 (24) : 4219 - 4222
[5] THE RABBIT LIVER MICROSOMAL BIOTRANSFORMATION OF 1,1-DIALKYLETHYLENES - ENANTIOFACE SELECTION OF EPOXIDATION AND ENANTIOSELECTIVITY OF EPOXIDE HYDROLYSIS
BELLUCCI, G
CHIAPPE, C
CORDONI, A
MARIONI, F
[J]. CHIRALITY, 1994, 6 (03) : 207 - 212
[6] PRODUCT ENANTIOSELECTIVITY OF THE MICROSOMAL AND CYTOSOLIC EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF MESO EPOXIDES
BELLUCCI, G
CAPITANI, I
CHIAPPE, C
MARIONI, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) : 1170 - 1171
[7] REGIOSELECTIVITY AND ENANTIOSELECTIVITY OF THE CYTOSOLIC EPOXIDE HYDROLASE-CATALYZED HYDROLYSIS OF RACEMIC MONOSUBSTITUTED ALKYLOXIRANES
BELLUCCI, G
CHIAPPE, C
MARIONI, F
BENETTI, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 361 - 363
[8] BELLUCCI G, 1995, IN PRESS J ORG CHEM
[9] BELLUCCI G, 1989, J ORG CHEM, V54, P5878
[10] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT
CIEPLAK, AS
TAIT, BD
JOHNSON, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) : 8447 - 8462

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