Reactivity of mononuclear alkylperoxo copper(II) complex. O-O bond cleavage and C-H bond activation

被引：99

作者：

Kunishita, Atsushi ^{[1
]}

Ishimaru, Hirohito ^{[2
]}

Nakashima, Satoru ^{[2
]}

Ogura, Takashi ^{[2
]}

Itoh, Shinobu ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan

[2] Univ Hyogo, Grad Sch Life Sci, Picobiol Res Ctr, Kamigori Cho, Hyogo 6781297, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 13期

关键词：

D O I：

10.1021/ja800443s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A detailed reactivity study has been carded out for the first time on a new mononuclear alkylperoxo copper(II) complex, which is generated by the reaction of copper(II) complex supported by the bis(pyridylmethyl)amine tridentate ligand containing a phenyl group at the 6-position of the pyridine donor groups and cumene hydroperoxide (CmOOH) in CH3CN. The cumylperoxo copper(II) complex thus obtained has been found to undergo homolytic cleavage of the O-O bond and induce C-H bond activation of exogenous substrates, providing important insights into the catalytic mechanism of copper monooxygenases.

引用

页码：4244 / +

页数：3

共 33 条

[1] ROLES OF PROXIMAL LIGAND IN HEME-PROTEINS - REPLACEMENT OF PROXIMAL HISTIDINE OF HUMAN MYOGLOBIN WITH CYSTEINE AND TYROSINE BY SITE-DIRECTED MUTAGENESIS AS MODELS FOR P-450, CHLOROPEROXIDASE, AND CATALASE [J].

ADACHI, S ;

NAGANO, S ;

ISHIMORI, K ;

WATANABE, Y ;

MORISHIMA, I ;

EGAWA, T ;

KITAGAWA, T ;

MAKINO, R .

BIOCHEMISTRY, 1993, 32 (01) :241-252

[2] SOLVENT EFFECTS ON THE COMPETITIVE BETA-SCISSION AND HYDROGEN-ATOM ABSTRACTION REACTIONS OF THE CUMYLOXYL RADICAL - RESOLUTION OF A LONG-STANDING PROBLEM [J].

AVILA, DV ;

BROWN, CE ;

INGOLD, KU ;

LUSZTYK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :466-470

[3] The hydrogen peroxide reactivity of peptidylglycine monooxygenase supports a Cu(II)-superoxo catalytic intermediate [J].

Bauman, AT ;

Yukl, ET ;

Alkevich, K ;

McCormack, AL ;

Blackburn, NJ .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (07) :4190-4198

[4] Spectroscopic and theoretical studies of mononuclear copper(II) alkyl- and hydroperoxo complexes: Electronic structure contributions to reactivity [J].

Chen, P ;

Fujisawa, K ;

Solomon, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10177-10193

[5] Oxygen activation by the noncoupled binuclear copper site in peptidylglycine α-hydroxylating monooxygenase.: Reaction mechanism and role of the noncoupled nature of the active site [J].

Chen, P ;

Solomon, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4991-5000

[6] Copper(II)-mediated aromatic ortho-hydroxylation:: A hybrid DFT and ab initio exploration [J].

Comba, Peter ;

Knoppe, Stefan ;

Martin, Bodo ;

Rajaraman, Gopalan ;

Rolli, Claudio ;

Shapiro, Brett ;

Stork, Timon .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) :344-357

[7] Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates [J].

Costas, M ;

Mehn, MP ;

Jensen, MP ;

Que, L .

CHEMICAL REVIEWS, 2004, 104 (02) :939-986

[8] Evidence that dioxygen and substrate activation are tightly coupled in dopamine β-monooxygenase -: Implications for the reactive oxygen species [J].

Evans, JP ;

Ahn, K ;

Klinman, JP .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (50) :49691-49698

[9] Investigation of the pathway for inter-copper electron transfer in peptidyglycine α-amidating monooxygenase [J].

Francisco, WA ;

Wille, G ;

Smith, AJ ;

Merkler, DJ ;

Klinman, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (41) :13168-13169

[10]

FUJII T, 2008, DALTON T, V164, P170

← 1 2 3 4 →