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Volumn 26, Issue 1, 2012, Pages 51-60

Identification of isomeric spin adducts of Leu-Tyr and Tyr-Leu free radicals using liquid chromatography-tandem mass spectrometry

Author keywords

DMPO; Mass spectrometry; Oxidation hydroxyl radical; Peptide; Spin trapping

Indexed keywords

AMINO ACIDS; CARBON; FREE RADICALS; LIQUID CHROMATOGRAPHY; OXIDATION; PEPTIDES; REACTION INTERMEDIATES;

EID: 83555174695     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1624     Document Type: Article
Times cited : (1)

References (46)
  • 1
    • 0344687267 scopus 로고    scopus 로고
    • Metal catalyzed oxidation of tyrosine residues by different oxidation systems of copper/hydrogen peroxide
    • Ali FE, Barnham KJ, Barrow CJ and Separovic F. Metal catalyzed oxidation of tyrosine residues by different oxidation systems of copper/hydrogen peroxide. Journal of Inorganic Biochemistry 2004; 98: 173-184.
    • (2004) Journal of Inorganic Biochemistry , vol.98 , pp. 173-184
    • Ali, F.E.1    Barnham, K.J.2    Barrow, C.J.3    Separovic, F.4
  • 2
    • 34248528663 scopus 로고    scopus 로고
    • EPR spin-trapping of protein radicals to investigate biological oxidative mechanisms
    • Augusto O and Muntz Vaz S. EPR spin-trapping of protein radicals to investigate biological oxidative mechanisms. Amino Acids 2007; 32: 535-542.
    • (2007) Amino Acids , vol.32 , pp. 535-542
    • Augusto, O.1    Muntz Vaz, S.2
  • 3
    • 0034122808 scopus 로고    scopus 로고
    • Do spin traps also act as classical chain-breaking antioxidants? A quantitative kinetic study of phenyl tert-butylnitrone (PBN) in solution and in liposomes
    • Barclay LR and Vinqvist MR. Do spin traps also act as classical chain-breaking antioxidants? A quantitative kinetic study of phenyl tert-butylnitrone (PBN) in solution and in liposomes. Free Radical Biology and Medicine 2000; 28: 1079-1090.
    • (2000) Free Radical Biology and Medicine , vol.28 , pp. 1079-1090
    • Barclay, L.R.1    Vinqvist, M.R.2
  • 4
    • 0029900542 scopus 로고    scopus 로고
    • ESR spin-trapping of a protein-derived tyrosyl radical from the reaction of cytochrome c with hydrogen peroxide
    • Barr DP, Gunther MR, Deterding LJ, Tomer KB and Mason RP. ESR spin-trapping of a protein-derived tyrosyl radical from the reaction of cytochrome c with hydrogen peroxide. Journal of Biological Chemistry 1996; 271: 15498-15503.
    • (1996) Journal of Biological Chemistry , vol.271 , pp. 15498-15503
    • Barr, D.P.1    Gunther, M.R.2    Deterding, L.J.3    Tomer, K.B.4    Mason, R.P.5
  • 7
    • 1642483018 scopus 로고    scopus 로고
    • Identification of free radicals on hemoglobin from its self-peroxidation using mass spectrometry and immuno-spin trapping: Observation of a histidinyl radical
    • Deterding LJ, Ramirez DC, Dubin JR, Mason RP and Tomer KB. Identification of free radicals on hemoglobin from its self-peroxidation using mass spectrometry and immuno-spin trapping: Observation of a histidinyl radical. Journal of Biological Chemistry 2004; 279: 11600-11607.
    • (2004) Journal of Biological Chemistry , vol.279 , pp. 11600-11607
    • Deterding, L.J.1    Ramirez, D.C.2    Dubin, J.R.3    Mason, R.P.4    Tomer, K.B.5
  • 8
    • 34548040476 scopus 로고    scopus 로고
    • Top-down and bottom-up mass spectrometric characterization of human myoglobin-centered free radicals induced by oxidative damage
    • Deterding LJ, Bhattacharjee S, Ramirez DC, Mason RP and Tomer KB. Top-down and bottom-up mass spectrometric characterization of human myoglobin-centered free radicals induced by oxidative damage. Analytical Chemistry 2007; 79: 6236-6248.
    • (2007) Analytical Chemistry , vol.79 , pp. 6236-6248
    • Deterding, L.J.1    Bhattacharjee, S.2    Ramirez, D.C.3    Mason, R.P.4    Tomer, K.B.5
  • 12
    • 0035877617 scopus 로고    scopus 로고
    • Mass spectral analysis of protein-based radicals using DBNBS. Nonradical adduct formation versus spin trapping
    • Filosa A and English AM. Mass spectral analysis of protein-based radicals using DBNBS. Nonradical adduct formation versus spin trapping. Journal of Biological Chemistry 2001; 276: 21022-21027.
    • (2001) Journal of Biological Chemistry , vol.276 , pp. 21022-21027
    • Filosa, A.1    English, A.M.2
  • 13
    • 66249093162 scopus 로고    scopus 로고
    • Reactivity of Tyr-Leu and Leu-Tyr dipeptides: identification of oxidation products by liquid chromatography-tandem mass spectrometry
    • Fonseca C, Domingues MR, Simoes C, Amado F and Domingues P. Reactivity of Tyr-Leu and Leu-Tyr dipeptides: identification of oxidation products by liquid chromatography-tandem mass spectrometry. Journal of Mass Spectrometry 2009; 44: 681-693.
    • (2009) Journal of Mass Spectrometry , vol.44 , pp. 681-693
    • Fonseca, C.1    Domingues, M.R.2    Simoes, C.3    Amado, F.4    Domingues, P.5
  • 14
    • 0031005562 scopus 로고    scopus 로고
    • Structural characterization of the products of hydroxyl-radical damage to leucine and their detection on proteins
    • Fu SL and Dean RT. Structural characterization of the products of hydroxyl-radical damage to leucine and their detection on proteins. Biochemical Journal 1997; 324: 41-48.
    • (1997) Biochemical Journal , vol.324 , pp. 41-48
    • Fu, S.L.1    Dean, R.T.2
  • 15
    • 0000302143 scopus 로고
    • Reaction-mechanisms in the radiolysis of peptides, polypeptides, and proteins
    • Garrison WM. Reaction-mechanisms in the radiolysis of peptides, polypeptides, and proteins. Chemical Reviews 1987; 87: 381-398.
    • (1987) Chemical Reviews , vol.87 , pp. 381-398
    • Garrison, W.M.1
  • 16
    • 0027389280 scopus 로고
    • Formation of peroxides in amino-acids and proteins exposed to oxygen free-radicals
    • Gebicki S and Gebicki JM. Formation of peroxides in amino-acids and proteins exposed to oxygen free-radicals. Biochemical Journal 1993; 289: 743-749.
    • (1993) Biochemical Journal , vol.289 , pp. 743-749
    • Gebicki, S.1    Gebicki, J.M.2
  • 17
    • 0042348012 scopus 로고    scopus 로고
    • Separation and identification of DMPO adducts of oxygen-centered radicals formed from organic hydroperoxides by LC-ESR, ESI-MS and MS/MS
    • Guo Q, Qian SY and Mason RP. Separation and identification of DMPO adducts of oxygen-centered radicals formed from organic hydroperoxides by LC-ESR, ESI-MS and MS/MS. Journal of the American Society for Mass Spectrometry 2003; 14: 862-871.
    • (2003) Journal of the American Society for Mass Spectrometry , vol.14 , pp. 862-871
    • Guo, Q.1    Qian, S.Y.2    Mason, R.P.3
  • 18
    • 0036909376 scopus 로고    scopus 로고
    • Determining the site of spin trapping of the equine myoglobin radical by combined use of EPR, electrophoretic purification, and mass spectrometry
    • Harris MN, Burchiel SW, Winyard PG, Engen JR, Mobarak CD and Timmins GS. Determining the site of spin trapping of the equine myoglobin radical by combined use of EPR, electrophoretic purification, and mass spectrometry. Chemical Research in Toxicology 2002; 15: 1589-1594.
    • (2002) Chemical Research in Toxicology , vol.15 , pp. 1589-1594
    • Harris, M.N.1    Burchiel, S.W.2    Winyard, P.G.3    Engen, J.R.4    Mobarak, C.D.5    Timmins, G.S.6
  • 19
    • 0035795180 scopus 로고    scopus 로고
    • Generation and propagation of radical reactions on proteins
    • Hawkins CL and Davies MJ. Generation and propagation of radical reactions on proteins. Biochimica Biophysica Acta 2001; 1504: 196-219.
    • (2001) Biochimica Biophysica Acta , vol.1504 , pp. 196-219
    • Hawkins, C.L.1    Davies, M.J.2
  • 20
    • 0036591861 scopus 로고    scopus 로고
    • Beta-scission of side-chain alkoxyl radicals on peptides and proteins results in the loss of side-chains as aldehydes and ketones
    • Headlam HA and Davies MJ. Beta-scission of side-chain alkoxyl radicals on peptides and proteins results in the loss of side-chains as aldehydes and ketones. Free Radical Biology and Medicine 2002; 32: 1171-1184.
    • (2002) Free Radical Biology and Medicine , vol.32 , pp. 1171-1184
    • Headlam, H.A.1    Davies, M.J.2
  • 21
    • 1842685103 scopus 로고    scopus 로고
    • Markers of protein oxidation: different oxidants give rise to variable yields of bound and released carbonyl products
    • Headlam HA and Davies MJ. Markers of protein oxidation: different oxidants give rise to variable yields of bound and released carbonyl products. Free Radical Biology and Medicine 2004; 36: 1175-1184.
    • (2004) Free Radical Biology and Medicine , vol.36 , pp. 1175-1184
    • Headlam, H.A.1    Davies, M.J.2
  • 22
    • 0033712060 scopus 로고    scopus 로고
    • Beta-scission of C-3 (beta-carbon) alkoxyl radicals on peptides and proteins: a novel pathway which results in the formation of alpha-carbon radicals and the loss of amino acid side chains
    • Headlam HA, Mortimer A, Easton CJ and Davies MJ. Beta-scission of C-3 (beta-carbon) alkoxyl radicals on peptides and proteins: a novel pathway which results in the formation of alpha-carbon radicals and the loss of amino acid side chains. Chemical Research in Toxicology 2000; 13: 1087-1095.
    • (2000) Chemical Research in Toxicology , vol.13 , pp. 1087-1095
    • Headlam, H.A.1    Mortimer, A.2    Easton, C.J.3    Davies, M.J.4
  • 24
    • 0029858111 scopus 로고    scopus 로고
    • Identification of radical adducts formed in the reactions of unsaturated fatty acids with soybean lipoxygenase using continuous flow fast atom bombardment with tandem mass spectrometry
    • Iwahashi H, Deterding LJ, Parker CE, Mason RP and Tomer KB. Identification of radical adducts formed in the reactions of unsaturated fatty acids with soybean lipoxygenase using continuous flow fast atom bombardment with tandem mass spectrometry. Free Radical Research 1996; 25: 255-274.
    • (1996) Free Radical Research , vol.25 , pp. 255-274
    • Iwahashi, H.1    Deterding, L.J.2    Parker, C.E.3    Mason, R.P.4    Tomer, K.B.5
  • 25
    • 0036388293 scopus 로고    scopus 로고
    • Electrochemically assisted Fenton reaction: reaction of hydroxyl radicals with xenobiotics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry
    • Jurva U, Wikstrom HV and Bruins AP. Electrochemically assisted Fenton reaction: reaction of hydroxyl radicals with xenobiotics followed by on-line analysis with high-performance liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry 2002; 16: 1934-1940.
    • (2002) Rapid Communications in Mass Spectrometry , vol.16 , pp. 1934-1940
    • Jurva, U.1    Wikstrom, H.V.2    Bruins, A.P.3
  • 26
    • 39149125741 scopus 로고    scopus 로고
    • Identifying the site of spin trapping in proteins by a combination of liquid chromatography, ELISA, and off-line tandem mass spectrometry
    • Lardinois OM, Detweiler CD, Tomer KB, Mason RP and Deterding LJ. Identifying the site of spin trapping in proteins by a combination of liquid chromatography, ELISA, and off-line tandem mass spectrometry. Free Radical Biology and Medicine 2008a; 44: 893-906.
    • (2008) Free Radical Biology and Medicine , vol.44 , pp. 893-906
    • Lardinois, O.M.1    Detweiler, C.D.2    Tomer, K.B.3    Mason, R.P.4    Deterding, L.J.5
  • 29
    • 33746906279 scopus 로고    scopus 로고
    • Detection of reactive free radicals derived from nucleosides by liquid chromatography coupled to tandem mass spectrometry of DMPO spin trapping adducts
    • Maurel V, Ravanat JL and Gambarelli S. Detection of reactive free radicals derived from nucleosides by liquid chromatography coupled to tandem mass spectrometry of DMPO spin trapping adducts. Rapid Communications in Mass Spectrometry 2006; 20: 2235-2242.
    • (2006) Rapid Communications in Mass Spectrometry , vol.20 , pp. 2235-2242
    • Maurel, V.1    Ravanat, J.L.2    Gambarelli, S.3
  • 30
    • 0032521011 scopus 로고    scopus 로고
    • The protein oxidation product 3,4-dihydroxyphenylalanine (DOPA) mediates oxidative DNA damage
    • Morin B, Davies MJ and Dean RT. The protein oxidation product 3, 4-dihydroxyphenylalanine (DOPA) mediates oxidative DNA damage. Biochemical Journal 1998; 330: 1059-1067.
    • (1998) Biochemical Journal , vol.330 , pp. 1059-1067
    • Morin, B.1    Davies, M.J.2    Dean, R.T.3
  • 31
    • 0035857421 scopus 로고    scopus 로고
    • Sites of hydroxyl radical reaction with amino acids identified by (2)H NMR detection of induced (1)H/(2)H exchange
    • Nukuna BN, Goshe MB and Anderson VE. Sites of hydroxyl radical reaction with amino acids identified by (2)H NMR detection of induced (1)H/(2)H exchange. Journal of the American Chemical Society 2001; 123: 1208-1214.
    • (2001) Journal of the American Chemical Society , vol.123 , pp. 1208-1214
    • Nukuna, B.N.1    Goshe, M.B.2    Anderson, V.E.3
  • 33
    • 0037090563 scopus 로고    scopus 로고
    • Identification of protein-derived tyrosyl radical in the reaction of cytochrome c and hydrogen peroxide: characterization by ESR spin-trapping, HPLC and MS
    • Qian SY, Chen YR, Deterding LJ, Fann YC, Chignell CF, Tomer KB and Mason RP. Identification of protein-derived tyrosyl radical in the reaction of cytochrome c and hydrogen peroxide: characterization by ESR spin-trapping, HPLC and MS. Biochemical Journal 2002; 363: 281-288.
    • (2002) Biochemical Journal , vol.363 , pp. 281-288
    • Qian, S.Y.1    Chen, Y.R.2    Deterding, L.J.3    Fann, Y.C.4    Chignell, C.F.5    Tomer, K.B.6    Mason, R.P.7
  • 34
    • 58249088828 scopus 로고    scopus 로고
    • Cu, Zn-superoxide dismutase-driven free radical modifications: copper- and carbonate radical anion-initiated protein radical chemistry
    • Ramirez DC, Gomez-Mejiba SE, Corbett JT, Deterding LJ, Tomer KB and Mason RP. Cu, Zn-superoxide dismutase-driven free radical modifications: copper- and carbonate radical anion-initiated protein radical chemistry. Biochemical Journal 2009; 417: 341-353.
    • (2009) Biochemical Journal , vol.417 , pp. 341-353
    • Ramirez, D.C.1    Gomez-Mejiba, S.E.2    Corbett, J.T.3    Deterding, L.J.4    Tomer, K.B.5    Mason, R.P.6
  • 35
    • 0033551437 scopus 로고    scopus 로고
    • Effects of structure on C-alpha-H bond enthalpies of amino acid residues: relevance to H transfers in enzyme mechanisms and in protein oxidation
    • Rauk A, Yu D, Taylor J, Shustov GV, Block DA and Armstrong DA. Effects of structure on C-alpha-H bond enthalpies of amino acid residues: relevance to H transfers in enzyme mechanisms and in protein oxidation. Biochemistry 1999; 38: 9089-9096.
    • (1999) Biochemistry , vol.38 , pp. 9089-9096
    • Rauk, A.1    Yu, D.2    Taylor, J.3    Shustov, G.V.4    Block, D.A.5    Armstrong, D.A.6
  • 37
    • 2542498043 scopus 로고    scopus 로고
    • Identification by electrospray tandem mass spectrometry of spin-trapped free radicals from oxidized 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine
    • Reis A, Domingues P, Ferrer-Correia AJV and Domingues MRM. Identification by electrospray tandem mass spectrometry of spin-trapped free radicals from oxidized 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine. Rapid Communications in Mass Spectrometry 2004; 18: 1047-1058.
    • (2004) Rapid Communications in Mass Spectrometry , vol.18 , pp. 1047-1058
    • Reis, A.1    Domingues, P.2    Ferrer-Correia, A.J.V.3    Domingues, M.R.M.4
  • 38
    • 31344465693 scopus 로고    scopus 로고
    • Identification of linoleic acid free radicals and other breakdown products using spin trapping with liquid chromatography-electrospray tandem mass spectrometry
    • Reis A, Domingues MRM, Amado FML, Ferrer-Correia AJV and Domingues P. Identification of linoleic acid free radicals and other breakdown products using spin trapping with liquid chromatography-electrospray tandem mass spectrometry. Biomedical Chromatography 2006; 20: 109-118.
    • (2006) Biomedical Chromatography , vol.20 , pp. 109-118
    • Reis, A.1    Domingues, M.R.M.2    Amado, F.M.L.3    Ferrer-Correia, A.J.V.4    Domingues, P.5
  • 40
    • 33746260405 scopus 로고    scopus 로고
    • Effects of anion proximity in peptide primary sequence on the rate and mechanism of leucine oxidation
    • Sharp JS and Tomer KB. Effects of anion proximity in peptide primary sequence on the rate and mechanism of leucine oxidation. Anal Chem 2006; 78: 4885-4893.
    • (2006) Anal Chem , vol.78 , pp. 4885-4893
    • Sharp, J.S.1    Tomer, K.B.2
  • 42
    • 0031010333 scopus 로고    scopus 로고
    • Reactive oxygen-mediated protein oxidation in aging and disease
    • Stadtman ER and Berlett BS. Reactive oxygen-mediated protein oxidation in aging and disease. Chemical Research in Toxicology 1997; 10: 485-494.
    • (1997) Chemical Research in Toxicology , vol.10 , pp. 485-494
    • Stadtman, E.R.1    Berlett, B.S.2
  • 43
    • 0346100345 scopus 로고    scopus 로고
    • Free radical-mediated oxidation of free amino acids and amino acid residues in proteins
    • Stadtman ER and Levine RL. Free radical-mediated oxidation of free amino acids and amino acid residues in proteins. Amino Acids 2003; 25: 207-218.
    • (2003) Amino Acids , vol.25 , pp. 207-218
    • Stadtman, E.R.1    Levine, R.L.2
  • 44
    • 0000023210 scopus 로고    scopus 로고
    • Thermochemical stability of alpha-amino-alpha-carbonylmethyl radicals and their resonance as measured by ESR
    • Welle FM, Beckhaus HD and Ruchardt C. Thermochemical stability of alpha-amino-alpha-carbonylmethyl radicals and their resonance as measured by ESR. Journal of Organic Chemistry 1997; 62: 552-558.
    • (1997) Journal of Organic Chemistry , vol.62 , pp. 552-558
    • Welle, F.M.1    Beckhaus, H.D.2    Ruchardt, C.3
  • 45
    • 33748774117 scopus 로고    scopus 로고
    • Effect of side chains on competing pathways for beta-scission reactions of peptide-backbone alkoxyl radicals
    • Wood GP, Easton CJ, Rauk A, Davies MJ and Radom L. Effect of side chains on competing pathways for beta-scission reactions of peptide-backbone alkoxyl radicals. J Phys Chem A 2006; 110: 10316-10323.
    • (2006) J Phys Chem A , vol.110 , pp. 10316-10323
    • Wood, G.P.1    Easton, C.J.2    Rauk, A.3    Davies, M.J.4    Radom, L.5
  • 46
    • 34548337296 scopus 로고    scopus 로고
    • Hydroxyl radical-mediated modification of proteins as probes for structural proteomics
    • Xu G and Chance MR. Hydroxyl radical-mediated modification of proteins as probes for structural proteomics. Chem Rev 2007; 107: 3514-3543.
    • (2007) Chem Rev , vol.107 , pp. 3514-3543
    • Xu, G.1    Chance, M.R.2


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