Heme/O2/•NO Nitric Oxide Dioxygenase (NOD) Reactivity: Phenolic Nitration via a Putative Heme-Peroxynitrite Intermediate

被引：66

作者：

Schopfer, Mark P. ^{[1
]}

Mondal, Biplab ^{[1
]}

Lee, Dong-Heon ^{[2
,3
]}

Sarjeant, Amy A. N. ^{[1
]}

Karlin, Kenneth D. ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

[2] Chonbuk Natl Univ, Dept Chem, Jeonju, South Korea

[3] Chonbuk Natl Univ, Res Inst Phys & Chem, Jeonju, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 32期

关键词：

SUPEROXIDE-DISMUTASE; TYROSINE NITRATION; MEDIATED OXIDATION; MECHANISM; MYOGLOBIN; HEMOGLOBIN; PORPHYRINS; COMPLEXES; MANGANESE; PATHOPHYSIOLOGY;

D O I：

10.1021/ja904832j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F-8)Fe-III-(O-2(center dot-)) (2) (F-8 = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (center dot NO; nitric oxide) to produce a nitrato-iron(III) compound (F-8)Fe-III-(NO3-) (3) (X-ray). The chemistry mimics the action of center dot NO Dioxygenases (NODS), microbial and mammalian heme proteins which facilitate center dot NO detoxification/homeostasis. A peroxynitrite intermediate complex is implicated; if 2,4-di-tert-butylphenol is added prior to center dot NO reaction with 2, o-nitration occurs giving 2,4-di-tert-butyl-6-nitrophenol. The iron product is (F-8)Fe-III-(OH) (4). The results suggest that heme/O-2/center dot NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.

引用

页码：11304 / +

页数：4

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