SYNTHETIC HEMES AS MIMICS FOR HIGH-VALENT INTERMEDIATES IN HEMOPROTEIN CATALYZED OXIDATIONS - SYNTHESIS AND OXIDATION OF CHLORO-7,8,17,18-TETRACYANO-5,10,15,20-TETRAPHENYLPORPHYRINATOIRON(III), A HEME WHICH CONTAINS STRONGLY ELECTRON-WITHDRAWING GROUPS IN THE BETA-PYRROLE POSITIONS

被引：9

作者：

ATKINSON, ST ^{[1
]}

BRADY, SP ^{[1
]}

JAMES, JP ^{[1
]}

NOLAN, KB ^{[1
]}

机构：

[1] DUBLIN CITY UNIV,SCH CHEM SCI,DUBLIN 9,IRELAND

来源：

PURE AND APPLIED CHEMISTRY | 1995年 / 67卷 / 07期

关键词：

D O I：

10.1351/pac199567071109

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The haem chloro-7,8,17,18-tetracyano-5,10,15,20-tetraphenylporphyrinato-iron(III), which contains strongly electron withdrawing groups in the beta-pyrrole positions, has been synthesised as a possible substrate for oxidations which mimic the formation of high valent haems in peroxidase and cytochrome p-450 catalysed reactions. The porphyrin was synthesised by reacting the copper(II) complex of the corresponding tetrabromoporphyrin with CuCN in quinoline. Treatment of the haem with m-chloroperbenzoic acid gave an oxidation product which is stable in solution at room temperature.

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页码：1109 / 1116

页数：8

相关论文

共 17 条

[1]

CALLOT HJ, 1974, B SOC CHIM FR II-CH, P1492

[2] REGIOSPECIFIC INTRODUCTION OF 4 SUBSTITUENTS TO PORPHYRIN SYSTEMS AT ANTIPODAL PYRROLENIC POSITIONS [J].

CROSSLEY, MJ ;

BURN, PL ;

CHEW, SS ;

CUTTANCE, FB ;

NEWSOM, IA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1564-1566

[3] SYNTHETIC PORPHYRINS METALLOPORPHYRINS WHICH MIMIC STATES IN CATALYTIC CYCLE OF CYTOCHROME-P-450 AND PEROXIDASES [J].

DAEID, NN ;

ATKINSON, ST ;

NOLAN, KB .

PURE AND APPLIED CHEMISTRY, 1993, 65 (07) :1541-1548

[4]

DAEID NN, 1993, INORG CHIM ACTA, V211, P55

[5] COMPOUNDS I OF CATALASE AND HORSE RADISH PEROXIDASE - PI-CATION RADICALS [J].

DOLPHIN, D ;

FORMAN, A ;

BORG, DC ;

FAJER, J ;

FELTON, RH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1971, 68 (03) :614-&

[6] STRUCTURE AND PROPERTIES OF MU-OXO-BIS(TETRAPHENYLPORPHINEIRON(3) [J].

FLEISCHER, EB ;

SRIVASTAVA, TS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (09) :2403-+

[7] EFFECTS OF THE ELECTRON-WITHDRAWING POWER OF SUBSTITUENTS ON THE ELECTRONIC-STRUCTURE AND REACTIVITY IN OXOIRON(IV) PORPHYRIN PI-CATION RADICAL COMPLEXES [J].

FUJII, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4641-4648

[8] OXOFERRYL COMPLEXES OF THE HALOGENATED (PORPHINATO)IRON CATALYST - (TETRAKIS(2,6-DICHLOROPHENYL)PORPHINATO)IRON [J].

GOLD, A ;

JAYARAJ, K ;

DOPPELT, P ;

WEISS, R ;

CHOTTARD, G ;

BILL, E ;

DING, X ;

TRAUTWEIN, AX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5756-5761

[9] 5,10,15,20-MESOTETRAKIS(3,5-DI-T-BUTYL-4-QUINOMETHIDE)PORPHYRINOGEN - A HIGHLY PUCKERED TETRAPYRROLIC MACROCYCLE FROM THE FACILE AERIAL OXIDATION OF A PHENOLIC PORPHYRIN [J].

GOLDER, AJ ;

MILGROM, LR ;

NOLAN, KB ;

POVEY, DC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) :1751-1753

[10] REACTIVE IRON PORPHYRIN DERIVATIVES RELATED TO THE CATALYTIC CYCLES OF CYTOCHROME-P-450 AND PEROXIDASE - STUDIES OF THE MECHANISM OF OXYGEN ACTIVATION [J].

GROVES, JT ;

WATANABE, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) :8443-8452