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Volumn 119, Issue 23, 2015, Pages 6885-6893

Toward an Understanding of the Oxidation Process of Methionine Enkephalin: A Combined Electrochemistry, Quantum Chemistry and Quantum Chemical Topology Analysis

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHEMICAL ANALYSIS; CONFORMATIONS; CYCLIC VOLTAMMETRY; ELECTRON TRANSITIONS; ELECTRONS; FREE RADICAL REACTIONS; FREE RADICALS; OXIDATION; QUANTUM CHEMISTRY; REDOX REACTIONS; TOPOLOGY;

EID: 84935899266     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b01207     Document Type: Article
Times cited : (7)

References (40)
  • 1
    • 36048968149 scopus 로고    scopus 로고
    • Targeting of Opioid-Producing Leukocytes for Pain Control
    • Machelska, H. Targeting of Opioid-Producing Leukocytes for Pain Control Neuropeptides 2007, 41, 355 - 363
    • (2007) Neuropeptides , vol.41 , pp. 355-363
    • Machelska, H.1
  • 2
    • 0141672033 scopus 로고    scopus 로고
    • Increased Striatal pre-Proenkephalin B Expression is Associated with Dyskinesia in Parkinson's Disease
    • Henry, B.; Duty, S.; Fox, S. H.; Crossman, A. R.; Brotchie, J. M. Increased Striatal pre-Proenkephalin B Expression is Associated with Dyskinesia in Parkinson's Disease Exp. Neurol. 2003, 183, 458 - 468
    • (2003) Exp. Neurol. , vol.183 , pp. 458-468
    • Henry, B.1    Duty, S.2    Fox, S.H.3    Crossman, A.R.4    Brotchie, J.M.5
  • 3
    • 65849395509 scopus 로고    scopus 로고
    • Enkephalinase Inhibitors: Potential Agents for the Management of Pain
    • Thanavala, V.; Kadam, V. J.; Ghosh, R. Enkephalinase Inhibitors: Potential Agents for the Management of Pain Curr. Drug Targets 2008, 9, 887 - 894
    • (2008) Curr. Drug Targets , vol.9 , pp. 887-894
    • Thanavala, V.1    Kadam, V.J.2    Ghosh, R.3
  • 4
    • 43649101960 scopus 로고    scopus 로고
    • Peripherally-Acting Opioids
    • Smith, H. S. Peripherally-Acting Opioids Pain Physician 2008, 11, S121 - S132
    • (2008) Pain Physician , vol.11 , pp. S121-S132
    • Smith, H.S.1
  • 6
    • 1942504811 scopus 로고    scopus 로고
    • The Function and Characteristics of Tyrosyl Radical Cofactors
    • Hoganson, C. W.; Tommos, C. The Function and Characteristics of Tyrosyl Radical Cofactors Biochim. Biophys. Acta 2004, 1655, 116 - 122
    • (2004) Biochim. Biophys. Acta , vol.1655 , pp. 116-122
    • Hoganson, C.W.1    Tommos, C.2
  • 7
    • 80455129436 scopus 로고    scopus 로고
    • Electrochemical and Structural Properties of a Protein System Designed to Generate Tyrosine Pourbaix Diagrams
    • Martinez-Rivera, M. C.; Berry, B. W.; Valentine, K. G.; Westerlund, K.; Hay, S.; Tommos, C. Electrochemical and Structural Properties of a Protein System Designed to Generate Tyrosine Pourbaix Diagrams J. Am. Chem. Soc. 2011, 133, 17786 - 17795
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 17786-17795
    • Martinez-Rivera, M.C.1    Berry, B.W.2    Valentine, K.G.3    Westerlund, K.4    Hay, S.5    Tommos, C.6
  • 8
    • 84862536489 scopus 로고    scopus 로고
    • Reversible Voltammograms and a Pourbaix Diagram for a Protein Tyrosine Radical
    • Berry, B. W.; Martinez-Rivera, M. C.; Tommos, C. Reversible Voltammograms and a Pourbaix Diagram for a Protein Tyrosine Radical Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 9739 - 9743
    • (2012) Proc. Natl. Acad. Sci. U.S.A. , vol.109 , pp. 9739-9743
    • Berry, B.W.1    Martinez-Rivera, M.C.2    Tommos, C.3
  • 10
    • 78651262855 scopus 로고    scopus 로고
    • Characterization by Mass Spectrometry and IRMPD Spectroscopy of the Sulfoxide Group in Oxidized Methionine and Related Compounds
    • Ignasiak, M.; Scuderi, D.; de Oliveira, P.; Pedzinski, T.; Rayah, Y.; Houee Levin, C. Characterization by Mass Spectrometry and IRMPD Spectroscopy of the Sulfoxide Group in Oxidized Methionine and Related Compounds Chem. Phys. Lett. 2011, 502, 29 - 36
    • (2011) Chem. Phys. Lett. , vol.502 , pp. 29-36
    • Ignasiak, M.1    Scuderi, D.2    De Oliveira, P.3    Pedzinski, T.4    Rayah, Y.5    Houee Levin, C.6
  • 11
    • 1242333091 scopus 로고    scopus 로고
    • Structural Properties and Topological Characterization of the Three-Electron Bond: The SO Radicals
    • Fourré, I.; Bergès, J. Structural Properties and Topological Characterization of the Three-Electron Bond: the SO Radicals J. Phys. Chem. A 2004, 108, 898 - 906
    • (2004) J. Phys. Chem. A , vol.108 , pp. 898-906
    • Fourré, I.1    Bergès, J.2
  • 12
    • 37049084998 scopus 로고
    • OH Radical Induced Decarboxylation of γ-Glutamylmethionine and S-Alkylglutathione Derivatives: Evidence for Two Different Pathways Involving C- and N-Terminal Decarboxylation
    • Bobrowski, K.; Schoneich, C.; Holcman, J.; Asmus, K. D. OH Radical Induced Decarboxylation of γ-Glutamylmethionine and S-Alkylglutathione Derivatives: Evidence for Two Different Pathways Involving C- and N-Terminal Decarboxylation J. Chem. Soc., Perkin Trans. 2 1991, 353 - 362
    • (1991) J. Chem. Soc., Perkin Trans. 2 , pp. 353-362
    • Bobrowski, K.1    Schoneich, C.2    Holcman, J.3    Asmus, K.D.4
  • 13
    • 0343725832 scopus 로고    scopus 로고
    • Decarboxylation Mechanism of the N-Terminal Glutamyl Moiety in γ-Glutamic Acid and Methionine Containing Peptides
    • Bobrowski, K.; Schoneich, C. Decarboxylation Mechanism of the N-Terminal Glutamyl Moiety in γ-Glutamic Acid and Methionine Containing Peptides Radiat. Phys. Chem. 1996, 47, 507 - 510
    • (1996) Radiat. Phys. Chem. , vol.47 , pp. 507-510
    • Bobrowski, K.1    Schoneich, C.2
  • 14
    • 54049100012 scopus 로고    scopus 로고
    • Stabilization and Reactions of Sulfur Radical Cations: Relevance to One-Electron Oxidation of Methionine in Peptides and Proteins
    • Bobrowski, K.; Houée-Levin, C.; Marciniak, B. Stabilization and Reactions of Sulfur Radical Cations: Relevance to One-Electron Oxidation of Methionine in Peptides and Proteins Chimia 2008, 62, 728 - 734
    • (2008) Chimia , vol.62 , pp. 728-734
    • Bobrowski, K.1    Houée-Levin, C.2    Marciniak, B.3
  • 15
    • 4344677922 scopus 로고    scopus 로고
    • Decreased Proteolysis Caused by Protein Aggregates, Inclusion Bodies, Plaques, Lipofuscin, Ceroid, and 'Aggresomes' during Oxidative Stress, Aging, and Disease
    • Grune, T.; Jung, T.; Merker, K.; Davies, K. J. Decreased Proteolysis Caused by Protein Aggregates, Inclusion Bodies, Plaques, Lipofuscin, Ceroid, and 'Aggresomes' during Oxidative Stress, Aging, and Disease Int. J. Biochem. Cell Biol. 2004, 36, 2519 - 2530
    • (2004) Int. J. Biochem. Cell Biol. , vol.36 , pp. 2519-2530
    • Grune, T.1    Jung, T.2    Merker, K.3    Davies, K.J.4
  • 18
    • 84890129027 scopus 로고    scopus 로고
    • Oxidation of Methionine-Containing Peptides by OH Radicals: Is Sulfoxide the Only Product? Study by Mass Spectrometry and IRMPD Spectroscopy
    • Ignasiak, M. T.; de Oliveira, P.; Houée Levin, C.; Scuderi, D. Oxidation of Methionine-Containing Peptides by OH Radicals: Is Sulfoxide the Only Product? Study by Mass Spectrometry and IRMPD Spectroscopy Chem. Phys. Lett. 2013, 590, 35 - 40
    • (2013) Chem. Phys. Lett. , vol.590 , pp. 35-40
    • Ignasiak, M.T.1    De Oliveira, P.2    Houée Levin, C.3    Scuderi, D.4
  • 19
    • 79952027571 scopus 로고    scopus 로고
    • Oxidation of Protein Tyrosine or Methionine Residues: From the Amino Acid to the Peptide
    • Bergès, J.; Trouillas, P.; Houée-Levin, C. Oxidation of Protein Tyrosine or Methionine Residues: From the Amino Acid to the Peptide J. Phys. Conf. Ser. 2011, 261, 012003
    • (2011) J. Phys. Conf. Ser. , vol.261 , pp. 012003
    • Bergès, J.1    Trouillas, P.2    Houée-Levin, C.3
  • 20
    • 79952011347 scopus 로고    scopus 로고
    • Towdards Understanding the Protein Oxidation Processes. OH Addition on Tyrosine, Phenylalanine or Methionine
    • Trouillas, P.; Bergès, J.; Houée-Levin, C. Towdards Understanding the Protein Oxidation Processes. OH Addition on Tyrosine, Phenylalanine or Methionine Int. J. Quantum Chem. 2011, 111, 143 - 151
    • (2011) Int. J. Quantum Chem. , vol.111 , pp. 143-151
    • Trouillas, P.1    Bergès, J.2    Houée-Levin, C.3
  • 21
    • 1542285304 scopus 로고    scopus 로고
    • A Multidimensional 1H NMR Investigation of the Conformation of Methionine-Enkephalin in Fast-Tumbling Bicelles
    • Marcotte, I.; Separovic, F.; Auger, M.; Gagne, S. M. A Multidimensional 1H NMR Investigation of the Conformation of Methionine-Enkephalin in Fast-Tumbling Bicelles Biophys. J. 2004, 86, 1587 - 1600
    • (2004) Biophys. J. , vol.86 , pp. 1587-1600
    • Marcotte, I.1    Separovic, F.2    Auger, M.3    Gagne, S.M.4
  • 22
    • 4344627663 scopus 로고    scopus 로고
    • An Application of Experimental Design Using Mutually Orthogonal Latin Squares in Conformational Studies of Peptides
    • Vengadesan, K.; Anbupalam, T.; Gautham, N. An Application of Experimental Design Using Mutually Orthogonal Latin Squares in Conformational Studies of Peptides Biopolymers 2004, 74, 476 - 494
    • (2004) Biopolymers , vol.74 , pp. 476-494
    • Vengadesan, K.1    Anbupalam, T.2    Gautham, N.3
  • 23
    • 0033104745 scopus 로고    scopus 로고
    • The Folding Funnel Landscape for the Peptide Met-Enkephalin
    • Hansmann, U. H.; Okamoto, Y.; Onuchic, J. N. The Folding Funnel Landscape for the Peptide Met-Enkephalin Proteins 1999, 34, 472 - 483
    • (1999) Proteins , vol.34 , pp. 472-483
    • Hansmann, U.H.1    Okamoto, Y.2    Onuchic, J.N.3
  • 24
    • 83955162897 scopus 로고    scopus 로고
    • Conformational Space Exploration of Met- and Leu-Enkephalin Using the MOLS Method, Molecular Dynamics, and Monte Carlo Simulation - A Comparative Study
    • Ramya, L.; Gautham, N. Conformational Space Exploration of Met- and Leu-Enkephalin Using the MOLS Method, Molecular Dynamics, and Monte Carlo Simulation - A Comparative Study Biopolymers 2012, 97, 165 - 176
    • (2012) Biopolymers , vol.97 , pp. 165-176
    • Ramya, L.1    Gautham, N.2
  • 25
    • 84864288909 scopus 로고    scopus 로고
    • Molecular Basis of Intramolecular Electron Transfer in Proteins during Radical-Mediated Oxidations: Computer Simulation Studies in Model Tyrosine-Cysteine Peptides in Solution
    • Petruk, A. A.; Bartesaghi, S.; Trujillo, M.; Estrin, D. A.; Murgida, D.; Kalyanaraman, B.; Marti, M. A.; Radi, R. Molecular Basis of Intramolecular Electron Transfer in Proteins during Radical-Mediated Oxidations: Computer Simulation Studies in Model Tyrosine-Cysteine Peptides in Solution Arch. Biochem. Biophys. 2012, 525, 82 - 91
    • (2012) Arch. Biochem. Biophys. , vol.525 , pp. 82-91
    • Petruk, A.A.1    Bartesaghi, S.2    Trujillo, M.3    Estrin, D.A.4    Murgida, D.5    Kalyanaraman, B.6    Marti, M.A.7    Radi, R.8
  • 26
    • 84904530301 scopus 로고    scopus 로고
    • Topological Analyses of Time-Dependent Electronic Structures: Application to Electron-Transfers in Methionine Enkephalin
    • Pilmé, J.; Luppi, E.; Bergès, J.; Houée Levin, C.; de la Lande, A. Topological Analyses of Time-Dependent Electronic Structures: Application to Electron-Transfers in Methionine Enkephalin J. Mol. Model. 2014, 20, 2368
    • (2014) J. Mol. Model. , vol.20 , pp. 2368
    • Pilmé, J.1    Luppi, E.2    Bergès, J.3    Houée Levin, C.4    De La Lande, A.5
  • 28
    • 84864952154 scopus 로고    scopus 로고
    • The One-Electron Reduction Potential of Methionine-Containing Peptides Depends on the Sequence
    • Bergès, J.; de Oliveira, P.; Fourré, I.; Houée Levin, C. The One-Electron Reduction Potential of Methionine-Containing Peptides Depends on the Sequence J. Phys. Chem. B 2012, 116, 9352 - 9362
    • (2012) J. Phys. Chem. B , vol.116 , pp. 9352-9362
    • Bergès, J.1    De Oliveira, P.2    Fourré, I.3    Houée Levin, C.4
  • 29
    • 84962359443 scopus 로고    scopus 로고
    • Accurate pKa Calculations for Carboxylic Acids Using Complete Basis Set and Gaussian-n Models Combined with CPCM Continuum Solvation Methods
    • Liptak, M. D.; Shields, G. C. Accurate p K a Calculations for Carboxylic Acids Using Complete Basis Set and Gaussian-n Models Combined with CPCM Continuum Solvation Methods J. Am. Chem. Soc. 2001, 123, 7314 - 7319
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7314-7319
    • Liptak, M.D.1    Shields, G.C.2
  • 30
    • 43949099654 scopus 로고    scopus 로고
    • Ab Initio and QM/MM Study of Electron Addition on the Disulfide Bond in Thioredoxin
    • Rickard, G. A.; Bergès, J.; Houée Levin, C.; Rauk, A. Ab Initio and QM/MM Study of Electron Addition on the Disulfide Bond in Thioredoxin J. Phys. Chem. B 2008, 112, 5774 - 5787
    • (2008) J. Phys. Chem. B , vol.112 , pp. 5774-5787
    • Rickard, G.A.1    Bergès, J.2    Houée Levin, C.3    Rauk, A.4
  • 31
    • 0027946619 scopus 로고
    • Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions
    • Silvi, B.; Savin, A. Classification of Chemical Bonds Based on Topological Analysis of Electron Localization Functions Nature 1994, 371, 683 - 686
    • (1994) Nature , vol.371 , pp. 683-686
    • Silvi, B.1    Savin, A.2
  • 33
    • 36549100412 scopus 로고
    • A Simple Measure of Electron Localization in Atomic and Molecular Systems
    • Becke, A. D.; Edgecombe, K. E. A Simple Measure of Electron Localization in Atomic and Molecular Systems J. Chem. Phys. 1990, 92, 5397 - 5403
    • (1990) J. Chem. Phys. , vol.92 , pp. 5397-5403
    • Becke, A.D.1    Edgecombe, K.E.2
  • 34
    • 18444395863 scopus 로고    scopus 로고
    • Time-dependent Electron Localization Function
    • Burnus, T.; Marques, M. A. L.; Gross, E. K. U. Time-dependent Electron Localization Function Phys. Rev. A 2005, 71, 010501 - 010504
    • (2005) Phys. Rev. A , vol.71 , pp. 010501-010504
    • Burnus, T.1    Marques, M.A.L.2    Gross, E.K.U.3
  • 35
    • 84855842287 scopus 로고    scopus 로고
    • Constrained Density Functional Theory
    • Kaduk, B.; Kowalczyk, T.; Van Voorhis, T. Constrained Density Functional Theory Chem. Rev. 2012, 112, 321 - 370
    • (2012) Chem. Rev. , vol.112 , pp. 321-370
    • Kaduk, B.1    Kowalczyk, T.2    Van Voorhis, T.3
  • 37
    • 0000598140 scopus 로고
    • Electron Transfer Reactions of Tryptophan and Tyrosine Derivatives
    • Jovanovic, S. V.; Harriman, A.; Simic, M. G. Electron Transfer Reactions of Tryptophan and Tyrosine Derivatives J. Phys. Chem. 1986, 90, 1935 - 1940
    • (1986) J. Phys. Chem. , vol.90 , pp. 1935-1940
    • Jovanovic, S.V.1    Harriman, A.2    Simic, M.G.3
  • 39
    • 7744239249 scopus 로고
    • Further Comments on the Redox Potentials of Tryptophan and Tyrosine
    • Harriman, A. Further Comments on the Redox Potentials of Tryptophan and Tyrosine J. Phys. Chem. 1987, 91, 6102 - 6104
    • (1987) J. Phys. Chem. , vol.91 , pp. 6102-6104
    • Harriman, A.1
  • 40
    • 0024384199 scopus 로고
    • Pulse Radiolytic Measurement of Redox Potentials: The Tyrosine and Tryptophan Radicals
    • DeFelippis, M. R.; Murthy, C. P.; Faraggi, M.; Klapper, M. H. Pulse Radiolytic Measurement of Redox Potentials: The Tyrosine and Tryptophan Radicals Biochemistry 1989, 28, 4847 - 4853
    • (1989) Biochemistry , vol.28 , pp. 4847-4853
    • DeFelippis, M.R.1    Murthy, C.P.2    Faraggi, M.3    Klapper, M.H.4


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