Heme/O2/•NO nitric oxide dioxygenase (NOD) reactivity: Phenolic nitration via a putative heme-peroxynitrite intermediate

Mark P. Schopfer; Biplab Mondal; Dong Heon Lee; Amy A.N. Sarjeant; Kenneth D. Karlin

doi:10.1021/ja904832j

Heme/O₂/•NO nitric oxide dioxygenase (NOD) reactivity: Phenolic nitration via a putative heme-peroxynitrite intermediate

Mark P. Schopfer
, Biplab Mondal
, Dong Heon Lee
, Amy A.N. Sarjeant
, Kenneth D. Karlin

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

69 Scopus citations

Abstract

(Chemical Equation Presented) An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F₈)Fe^III-(O₂ ^•-) (2) (F₈ = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (•NO; nitric oxide) to produce a nitrato-iron(III) compound (F₈)Fe^III-(NO ₃^-) (3) (X-ray). The chemistry mimics the action of •NO Dioxygenases (NODs), microbial and mammalian heme proteins which facilitate •NO detoxification/homeostasis. A peroxynitrite intermediate complex is implicated; if 2,4-di-tert-butylphenol is added prior to •NO reaction with 2, o-nitration occurs giving 2,4-di-tert-butyl-6-nitrophenol. The iron product is (F₈)Fe^III-(OH) (4). The results suggest that heme/O₂/•NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.

Original language	English
Pages (from-to)	11304-11305
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	32
DOIs	https://doi.org/10.1021/ja904832j
State	Published - 2009.08.19

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Engineering - Chemical
Chemistry
Biological Sciences

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10.1021/ja904832j

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@article{efd83741ce7f4615919610b6e53e0092,

title = "Heme/O2/•NO nitric oxide dioxygenase (NOD) reactivity: Phenolic nitration via a putative heme-peroxynitrite intermediate",

abstract = "(Chemical Equation Presented) An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F8)FeIII-(O2 •-) (2) (F8 = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (•NO; nitric oxide) to produce a nitrato-iron(III) compound (F8)FeIII-(NO 3-) (3) (X-ray). The chemistry mimics the action of •NO Dioxygenases (NODs), microbial and mammalian heme proteins which facilitate •NO detoxification/homeostasis. A peroxynitrite intermediate complex is implicated; if 2,4-di-tert-butylphenol is added prior to •NO reaction with 2, o-nitration occurs giving 2,4-di-tert-butyl-6-nitrophenol. The iron product is (F8)FeIII-(OH) (4). The results suggest that heme/O2/•NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.",

author = "Schopfer, \{Mark P.\} and Biplab Mondal and Lee, \{Dong Heon\} and Sarjeant, \{Amy A.N.\} and Karlin, \{Kenneth D.\}",

year = "2009",

month = aug,

day = "19",

doi = "10.1021/ja904832j",

language = "English",

volume = "131",

pages = "11304--11305",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

number = "32",

}

TY - JOUR

T1 - Heme/O2/•NO nitric oxide dioxygenase (NOD) reactivity

T2 - Phenolic nitration via a putative heme-peroxynitrite intermediate

AU - Schopfer, Mark P.

AU - Mondal, Biplab

AU - Lee, Dong Heon

AU - Sarjeant, Amy A.N.

AU - Karlin, Kenneth D.

PY - 2009/8/19

Y1 - 2009/8/19

N2 - (Chemical Equation Presented) An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F8)FeIII-(O2 •-) (2) (F8 = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (•NO; nitric oxide) to produce a nitrato-iron(III) compound (F8)FeIII-(NO 3-) (3) (X-ray). The chemistry mimics the action of •NO Dioxygenases (NODs), microbial and mammalian heme proteins which facilitate •NO detoxification/homeostasis. A peroxynitrite intermediate complex is implicated; if 2,4-di-tert-butylphenol is added prior to •NO reaction with 2, o-nitration occurs giving 2,4-di-tert-butyl-6-nitrophenol. The iron product is (F8)FeIII-(OH) (4). The results suggest that heme/O2/•NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.

AB - (Chemical Equation Presented) An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F8)FeIII-(O2 •-) (2) (F8 = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (•NO; nitric oxide) to produce a nitrato-iron(III) compound (F8)FeIII-(NO 3-) (3) (X-ray). The chemistry mimics the action of •NO Dioxygenases (NODs), microbial and mammalian heme proteins which facilitate •NO detoxification/homeostasis. A peroxynitrite intermediate complex is implicated; if 2,4-di-tert-butylphenol is added prior to •NO reaction with 2, o-nitration occurs giving 2,4-di-tert-butyl-6-nitrophenol. The iron product is (F8)FeIII-(OH) (4). The results suggest that heme/O2/•NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.

UR - https://www.scopus.com/pages/publications/68849084972

U2 - 10.1021/ja904832j

DO - 10.1021/ja904832j

M3 - Journal article

C2 - 19627146

AN - SCOPUS:68849084972

SN - 0002-7863

VL - 131

SP - 11304

EP - 11305

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 32

ER -

Heme/O₂/•NO nitric oxide dioxygenase (NOD) reactivity: Phenolic nitration via a putative heme-peroxynitrite intermediate

Abstract

Quacquarelli Symonds(QS) Subject Topics

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