MECHANISTIC STUDY OF A SYNTHETICALLY USEFUL MONOOXYGENASE MODEL USING THE HYPERSENSITIVE PROBE TRANS-2-PHENYL-1-VINYLCYCLOPROPANE

被引：79

作者：

FU, H

LOOK, GC

ZHANG, W

JACOBSEN, EN

WONG, CH

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

[2] UNIV ILLINOIS, DEPT CHEM, ROGER ADAMS LAB, URBANA, IL 61801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 23期

关键词：

D O I：

10.1021/jo00023a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of trans-2-phenyl-1-vinylcyclopropane as a hypersensitive probe to study the epoxidation mechanisms of monooxygenases and their models is described; the high yield epoxide formation indicates that the Mn(III) salen mediated epoxidation of unfunctionalized alkyl-substituted olefins is a concerted process. A stepwise mechanism, however, is suggested for the epoxidation of aryl-substituted olefins.

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收藏

页码：6497 / 6500

页数：4

相关论文

共 45 条

[1] CALIBRATION OF THE BICYCLO[2.1.0]PENT-2-YL RADICAL RING-OPENING AND AN OXYGEN REBOUND RATE-CONSTANT FOR CYTOCHROME-P-450 [J].

BOWRY, VW ;

LUSZTYK, J ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1927-1928

[2]

BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645

[3] INTERMEDIATES IN THE EPOXIDATION OF ALKENES BY CYTOCHROME-P-450 MODELS .2. USE OF THE TRANS-2,TRANS-3-DIPHENYLCYCLOPROPYL SUBSTITUENT IN A SEARCH FOR RADICAL INTERMEDIATES [J].

CASTELLINO, AJ ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7512-7519

[4] CARBENOID FORMATION OF ARYLCYCLOPROPANES FROM OLEFINS BENZAL BROMIDES + ORGANOLITHIUM COMPOUNDS + FROM PHOTOLYSIS OF ARYLDIAZOMETHANES [J].

CLOSS, GL ;

MOSS, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (19) :4042-&

[5] STEREOCHEMICAL AND MECHANISTIC STUDIES OF THE SUICIDE EVENT IN BIOMIMETIC P-450 OLEFIN EPOXIDATION [J].

COLLMAN, JP ;

HAMPTON, PD ;

BRAUMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7861-7862

[6] EPOXIDATION OF OLEFINS BY CYTOCHROME-P-450 MODEL COMPOUNDS - KINETICS AND STEREOCHEMISTRY OF OXYGEN ATOM TRANSFER AND ORIGIN OF SHAPE SELECTIVITY [J].

COLLMAN, JP ;

BRAUMAN, JI ;

MEUNIER, B ;

HAYASHI, T ;

KODADEK, T ;

RAYBUCK, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) :2000-2005

[7] EPOXIDATION OF OLEFINS BY CYTOCHROME-P-450 MODEL COMPOUNDS - MECHANISM OF OXYGEN ATOM TRANSFER [J].

COLLMAN, JP ;

BRAUMAN, JI ;

MEUNIER, B ;

RAYBUCK, SA ;

KODADEK, T .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-PHYSICAL SCIENCES, 1984, 81 (10) :3245-3248

[8]

COLLMAN JP, 1985, J AM CHEM SOC, V107, P4343

[9]

DEMONTELLANO PRO, 1987, J AM CHEM SOC, V109, P3415

[10] VINYLCYCLOPENTENE SYNTHESIS VIA PHENYLTHIO RADICAL CATALYZED ADDITION OF ELECTRON DEFICIENT ALKYNES TO SUBSTITUTED VINYLCYCLOPROPANES [J].

FELDMAN, KS ;

RUCKLE, RE ;

ROMANELLI, AL .

TETRAHEDRON LETTERS, 1989, 30 (43) :5845-5848

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