Literature DB >> 19627146

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

Mark P Schopfer1, Biplab Mondal, Dong-Heon Lee, Amy A N Sarjeant, Kenneth D Karlin.   

Abstract

An oxy-heme complex, the heme-superoxo species (tetrahydrofuran)(F(8))Fe(III)-(O(2)(*-)) (2) (F(8) = an ortho-difluoro substituted tetraarylporphyrinate), reacts with nitrogen monoxide (*NO; nitric oxide) to produce a nitrato-iron(III) compound (F(8))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 (F(8))Fe(III)-(OH) (4). The results suggest that heme/O(2)/*NO chemistry may lead to peroxynitrite leakage and/or exogenous substrate oxidative/nitrative reactivity.

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Year:  2009        PMID： 19627146      PMCID： PMC2747244          DOI： 10.1021/ja904832j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  34 in total

1.  Kinetic and mechanistic studies of the NO*-mediated oxidation of oxymyoglobin and oxyhemoglobin.

Authors:  S Herold; M Exner; T Nauser
Journal:  Biochemistry       Date:  2001-03-20       Impact factor: 3.162

2.  Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide.

Authors:  J S Beckman; T W Beckman; J Chen; P A Marshall; B A Freeman
Journal:  Proc Natl Acad Sci U S A       Date:  1990-02       Impact factor: 11.205

3.  (Nitro)Iron(III) Porphyrins. EPR Detection of a Transient Low-Spin Iron(III) Complex and Structural Characterization of an O Atom Transfer Product.

Authors:  Orde Q. Munro; W. Robert Scheidt
Journal:  Inorg Chem       Date:  1998-05-04       Impact factor: 5.165

4.  Kinetics and mechanism of *NO2 reacting with various oxidation states of myoglobin.

Authors:  Sara Goldstein; Gabor Merenyi; Amram Samuni
Journal:  J Am Chem Soc       Date:  2004-12-08       Impact factor: 15.419

5.  Mechanism of nitrosylmyoglobin autoxidation: temperature and oxygen pressure effects on the two consecutive reactions.

Authors:  Jens K S Møller; Leif H Skibsted
Journal:  Chemistry       Date:  2004-05-03       Impact factor: 5.236

6.  A theoretical study of myoglobin working as a nitric oxide scavenger.

Authors:  L Mattias Blomberg; Margareta R A Blomberg; Per E M Siegbahn
Journal:  J Biol Inorg Chem       Date:  2004-09-25       Impact factor: 3.358

7.  Molecular dynamics simulation of the HOONO decomposition and the HO*/NO2* caged radical pair in water.

Authors:  Hakan Gunaydin; K N Houk
Journal:  J Am Chem Soc       Date:  2008-07-10       Impact factor: 15.419

Review 8.  Peroxynitrite: biochemistry, pathophysiology and development of therapeutics.

Authors:  Csaba Szabó; Harry Ischiropoulos; Rafael Radi
Journal:  Nat Rev Drug Discov       Date:  2007-08       Impact factor: 84.694

9.  Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase.

Authors:  H Ischiropoulos; L Zhu; J Chen; M Tsai; J C Martin; C D Smith; J S Beckman
Journal:  Arch Biochem Biophys       Date:  1992-11-01       Impact factor: 4.013

10.  The millisecond intermediate in the reaction of nitric oxide with oxymyoglobin is an iron(III)--nitrato complex, not a peroxynitrite.

Authors:  Erik T Yukl; Simon de Vries; Pierre Moënne-Loccoz
Journal:  J Am Chem Soc       Date:  2009-06-03       Impact factor: 15.419
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  19 in total

1.  Isocyanide or nitrosyl complexation to hemes with varying tethered axial base ligand donors: synthesis and characterization.

Authors:  Savita K Sharma; Hyun Kim; Patrick J Rogler; Maxime A Siegler; Kenneth D Karlin
Journal:  J Biol Inorg Chem       Date:  2016-06-27       Impact factor: 3.358

2.  Photoinitiated Reactivity of a Thiolate-Ligated, Spin-Crossover Nonheme {FeNO}(7) Complex with Dioxygen.

Authors:  Alison C McQuilken; Hirotoshi Matsumura; Maximilian Dürr; Alex M Confer; John P Sheckelton; Maxime A Siegler; Tyrel M McQueen; Ivana Ivanović-Burmazović; Pierre Moënne-Loccoz; David P Goldberg
Journal:  J Am Chem Soc       Date:  2016-02-26       Impact factor: 15.419

3.  Direct Resonance Raman Characterization of a Peroxynitrito Copper Complex Generated from O2 and NO and Mechanistic Insights into Metal-Mediated Peroxynitrite Decomposition.

Authors:  Jeffrey J Liu; Maxime A Siegler; Kenneth D Karlin; Pierre Moënne-Loccoz
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-03       Impact factor: 15.336

4.  Nitrogen Oxide Atom-Transfer Redox Chemistry; Mechanism of NO(g) to Nitrite Conversion Utilizing μ-oxo Heme-Fe(III)-O-Cu(II)(L) Constructs.

Authors:  Shabnam Hematian; Isabell Kenkel; Tatyana E Shubina; Maximilian Dürr; Jeffrey J Liu; Maxime A Siegler; Ivana Ivanovic-Burmazovic; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2015-05-14       Impact factor: 15.419

5.  Copper(I)/NO(g) Reductive Coupling Producing a trans-Hyponitrite Bridged Dicopper(II) Complex: Redox Reversal Giving Copper(I)/NO(g) Disproportionation.

Authors:  Gayan B Wijeratne; Shabnam Hematian; Maxime A Siegler; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2017-09-12       Impact factor: 15.419

6.  A Six-Coordinate Peroxynitrite Low-Spin Iron(III) Porphyrinate Complex-The Product of the Reaction of Nitrogen Monoxide (·NO(g)) with a Ferric-Superoxide Species.

Authors:  Savita K Sharma; Andrew W Schaefer; Hyeongtaek Lim; Hirotoshi Matsumura; Pierre Moënne-Loccoz; Britt Hedman; Keith O Hodgson; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2017-11-21       Impact factor: 15.419

7.  Peroxynitrite chemistry derived from nitric oxide reaction with a Cu(II)-OOH species and a copper mediated NO reductive coupling reaction.

Authors:  Sunghee Kim; Maxime A Siegler; Kenneth D Karlin
Journal:  Chem Commun (Camb)       Date:  2013-12-09       Impact factor: 6.222

8.  Nitric oxide generation from heme/copper assembly mediated nitrite reductase activity.

Authors:  Shabnam Hematian; Maxime A Siegler; Kenneth D Karlin
Journal:  J Biol Inorg Chem       Date:  2014-01-16       Impact factor: 3.358

9.  A Peroxynitrite Dicopper Complex: Formation via Cu-NO and Cu-O2 Intermediates and Reactivity via O-O Cleavage Chemistry.

Authors:  Rui Cao; Lee Taylor Elrod; Ryan L Lehane; Eunsuk Kim; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2016-12-02       Impact factor: 15.419

10.  Reactions of a heme-superoxo complex toward a cuprous chelate and •NO(g): CcO and NOD chemistry.

Authors:  Savita K Sharma; Patrick J Rogler; Kenneth D Karlin
Journal:  J Porphyr Phthalocyanines       Date:  2015 Jan-Mar       Impact factor: 1.811
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