메뉴 건너뛰기




Volumn 17, Issue 10, 2004, Pages 1323-1328

Thiyl radical reaction with amino acid side chains: Rate constants for hydrogen transfer and relevance for posttranslational protein modification

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYSTEINE; PROTEIN; RADICAL; THIOL DERIVATIVE; THIYL RADICAL; UNCLASSIFIED DRUG;

EID: 6344249017     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049856y     Document Type: Article
Times cited : (73)

References (33)
  • 1
    • 6344222526 scopus 로고
    • (Packer, L., and Cadenas, E., Eds.), Marcel Dekker, New York
    • Wardman, P. (1995) In Reactions of Thiol Radicals (Packer, L., and Cadenas, E., Eds.) pp 1-19, Marcel Dekker, New York.
    • (1995) Reactions of Thiol Radicals , pp. 1-19
    • Wardman, P.1
  • 2
    • 0030601764 scopus 로고    scopus 로고
    • Oxygen is not required for degradation of DNA by glutathione and Cu(II)
    • Jain, A., Alvi, N. K., Parish, J. H., and Hadi, S. M. (1996) Oxygen is not required for degradation of DNA by glutathione and Cu(II). Mutat. Res. 357, 83-88.
    • (1996) Mutat. Res. , vol.357 , pp. 83-88
    • Jain, A.1    Alvi, N.K.2    Parish, J.H.3    Hadi, S.M.4
  • 3
    • 0028016446 scopus 로고
    • Characterization of baculovirus recombinant wild-type p53. Dimerization of p53 is requred for high-affinity DNA binding and cysteine oxidation inhibits p53 DNA binding
    • Delphin, C., Cahen, P., Lawrence, J. J., and Baudier, J. (1994) Characterization of baculovirus recombinant wild-type p53. Dimerization of p53 is requred for high-affinity DNA binding and cysteine oxidation inhibits p53 DNA binding. Eur. J. Biochem. 223, 683-692.
    • (1994) Eur. J. Biochem. , vol.223 , pp. 683-692
    • Delphin, C.1    Cahen, P.2    Lawrence, J.J.3    Baudier, J.4
  • 5
    • 0023138271 scopus 로고
    • The reverse of the 'repair' reaction of thiols: H-abstraction at carbon by thiyl radicals
    • Akhlaq, M. S., Schuchmann, H.-P., and von Sonntag, C. (1987) The reverse of the 'repair' reaction of thiols: H-abstraction at carbon by thiyl radicals. Int. J. Radiat. Biol. 51, 91-102.
    • (1987) Int. J. Radiat. Biol. , vol.51 , pp. 91-102
    • Akhlaq, M.S.1    Schuchmann, H.-P.2    Von Sonntag, C.3
  • 6
    • 0001248005 scopus 로고
    • Determination of absolute rate constants for the reversible hydrogen-atom transfer between thiyl radicals and alcohols or ethers
    • Schöneich, C., Asmus, K. D., and Bonifacic, M. (1995) Determination of absolute rate constants for the reversible hydrogen-atom transfer between thiyl radicals and alcohols or ethers. J. Chem. Soc. Faraday Trans. 91, 1923-1930.
    • (1995) J. Chem. Soc. Faraday Trans. , vol.91 , pp. 1923-1930
    • Schöneich, C.1    Asmus, K.D.2    Bonifacic, M.3
  • 7
    • 0035400112 scopus 로고    scopus 로고
    • Thiyl radicals abstract Hydrogen atoms from carbohydrates: Reactivity and selectivity
    • Pogocki, D., and Schöneich, C. (2001) Thiyl radicals abstract Hydrogen atoms from carbohydrates: reactivity and selectivity. Free Radical Biol. Med. 31, 98-107.
    • (2001) Free Radical Biol. Med. , vol.31 , pp. 98-107
    • Pogocki, D.1    Schöneich, C.2
  • 8
    • 0000407127 scopus 로고
    • Free-radical reactions involving thiols and disulphides
    • (Chatgilialoglu, C., and Asmus, K. D., Eds.), Plenum Press, New York
    • von Sonntag, C. (1990) Free-radical reactions involving thiols and disulphides. In Sulfur Centered Reactive Intermediates in Chemistry and Biology (Chatgilialoglu, C., and Asmus, K. D., Eds.) pp 359-366, Plenum Press, New York.
    • (1990) Sulfur Centered Reactive Intermediates in Chemistry and Biology , pp. 359-366
    • Von Sonntag, C.1
  • 9
    • 1842540158 scopus 로고    scopus 로고
    • Radicals in biomaterials
    • (Renaud, P., and Sibi, M. P., Eds.), Wiley-VCH, Weinheim, Germany
    • Easton, C. J. (2001) Radicals in biomaterials. In Radicals in Organic Synthesis, Vol. 2, Applications (Renaud, P., and Sibi, M. P., Eds.) pp 505-522, Wiley-VCH, Weinheim, Germany.
    • (2001) Radicals in Organic Synthesis, Vol. 2, Applications , vol.2 , pp. 505-522
    • Easton, C.J.1
  • 10
    • 0141513749 scopus 로고    scopus 로고
    • Thiyl radical reaction with thymine: Absolute rate constant for hydrogen abstraction and comparison to benzylic C-H bonds
    • Nauser, T., and Schöneich, C. (2003) Thiyl radical reaction with thymine: Absolute rate constant for hydrogen abstraction and comparison to benzylic C-H bonds. Chem. Res. Toxicol. 16, 1056-1061.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1056-1061
    • Nauser, T.1    Schöneich, C.2
  • 11
    • 0037467060 scopus 로고    scopus 로고
    • αC-H bonds in model peptides: Absolute rate constants and effect of amino acid structure
    • αC-H bonds in model peptides: Absolute rate constants and effect of amino acid structure. J. Am. Chem. Soc. 125, 2042-2043.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2042-2043
    • Nauser, T.1    Schöneich, C.2
  • 12
    • 84983725661 scopus 로고
    • Mechanistic deductions from solvent isotope effects
    • Schowen, R. L. (1972) Mechanistic deductions from solvent isotope effects. Prog. Phys. Org. Chem. 9, 275-332.
    • (1972) Prog. Phys. Org. Chem. , vol.9 , pp. 275-332
    • Schowen, R.L.1
  • 13
    • 0042697197 scopus 로고    scopus 로고
    • H-Atom abstraction by C-centered radicals from cyclic and acyclic dipeptides. A theoretical and experimental study of reaction rates
    • Reid, D. L., Arsmtrong, D. A., Rauk, A., Chandrasekhar, N., Schuchmann, M. N., Westhoff, U., and von Sonntag, C. (2003) H-Atom abstraction by C-centered radicals from cyclic and acyclic dipeptides. A theoretical and experimental study of reaction rates. Phys. Chem. Chem. Phys. 5, 3278-3288.
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 3278-3288
    • Reid, D.L.1    Arsmtrong, D.A.2    Rauk, A.3    Chandrasekhar, N.4    Schuchmann, M.N.5    Westhoff, U.6    Von Sonntag, C.7
  • 14
    • 0001336637 scopus 로고    scopus 로고
    • Anchimeric assistance in hydrogen atom transfer reactions on the side chains of amino acid derivatives
    • Easton, C. J., and Merrett, M. C. (1996) Anchimeric assistance in hydrogen atom transfer reactions on the side chains of amino acid derivatives. J. Am. Chem. Soc. 118, 3035-3036.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3035-3036
    • Easton, C.J.1    Merrett, M.C.2
  • 15
    • 0141797488 scopus 로고    scopus 로고
    • Notre Dame Radiation Laboratry-Radiation Chemistry Data Center. (2003) RCDC Kinetics Database. www.rcdc.nd.edu.
    • (2003) RCDC Kinetics Database
  • 16
    • 0001434308 scopus 로고
    • Kinetics of one-electron oxidation of thiols and hydrogen abstraction by thiyl radicals from α-amino C-H bonds
    • Zhao, R., Lind, J., Merényi, G., and Eriksen, T. E. (1994) Kinetics of one-electron oxidation of thiols and hydrogen abstraction by thiyl radicals from α-amino C-H bonds. J. Am. Chem. Soc. 116, 12010-12015.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12010-12015
    • Zhao, R.1    Lind, J.2    Merényi, G.3    Eriksen, T.E.4
  • 17
    • 0000302143 scopus 로고
    • Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins
    • Garrison, W. M. (1987) Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins. Chem. Rev. 87, 381-398.
    • (1987) Chem. Rev. , vol.87 , pp. 381-398
    • Garrison, W.M.1
  • 18
    • 33751158782 scopus 로고
    • Pulse radiolysis of 2-mercaptoethanol in oxygenated aqueous solutions: Generation and the reactions of the thiylperoxyl radical
    • Zhang, X., Zhang, N., Schuchmann H.-P., and von Sonntag, C. (1994) Pulse radiolysis of 2-mercaptoethanol in oxygenated aqueous solutions: Generation and the reactions of the thiylperoxyl radical. J. Phys. Chem. 98, 6541-6547.
    • (1994) J. Phys. Chem. , vol.98 , pp. 6541-6547
    • Zhang, X.1    Zhang, N.2    Schuchmann, H.-P.3    Von Sonntag, C.4
  • 19
    • 0000906512 scopus 로고
    • Hydrocarbon bond dissociation energies
    • McMillen, D. F., and Golden, D. M. (1982) Hydrocarbon bond dissociation energies. Annu. Rev. Phys. Chem. 33, 493-532.
    • (1982) Annu. Rev. Phys. Chem. , vol.33 , pp. 493-532
    • McMillen, D.F.1    Golden, D.M.2
  • 20
    • 0038005812 scopus 로고    scopus 로고
    • Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study
    • Lucarini, M., Mugnaini, V., Pedulli, G. F., and Guerra, M. (2003) Hydrogen-bonding effects on the properties of phenoxyl radicals. An EPR, kinetic, and computational study. J. Am. Chem. Soc. 125, 8318-8329.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8318-8329
    • Lucarini, M.1    Mugnaini, V.2    Pedulli, G.F.3    Guerra, M.4
  • 21
    • 0001193680 scopus 로고
    • Comparisons of the acidities and homolytic bond dissociation energies of the acidic nitrogen-hydrogen and carbon-hydrogen bonds in diphenylmethanes and carbazoles
    • Bordwell, F. G., Zhang, X., and Cheng, J. P. (1991) Comparisons of the acidities and homolytic bond dissociation energies of the acidic nitrogen-hydrogen and carbon-hydrogen bonds in diphenylmethanes and carbazoles. J. Org. Chem 56, 3216-3219.
    • (1991) J. Org. Chem. , vol.56 , pp. 3216-3219
    • Bordwell, F.G.1    Zhang, X.2    Cheng, J.P.3
  • 22
    • 0024317199 scopus 로고
    • Reversible H-atom abstraction from alcohols by thiyl radicals: Determination of absolute rate constants by pulse radiolysis
    • Schöneich, C., Bonifacic, M., and Asmus, K. D. (1989) Reversible H-atom abstraction from alcohols by thiyl radicals: Determination of absolute rate constants by pulse radiolysis. Free Radical Res. Commun. 6, 393-405.
    • (1989) Free Radical Res. Commun. , vol.6 , pp. 393-405
    • Schöneich, C.1    Bonifacic, M.2    Asmus, K.D.3
  • 23
    • 0002103490 scopus 로고
    • Hydrogen abstraction by thiyl radicals from activated C-H bonds of alcohols, ethers and polyunsaturated fatty acids
    • (Chatgilialoglu, C., and Asmus, K. D., Eds.), Plenum Press, New York
    • Schöneich, C., Bonifacic, M., Dillinger, U., and Asmus, K. D. (1990) Hydrogen abstraction by thiyl radicals from activated C-H bonds of alcohols, ethers and polyunsaturated fatty acids. In Sulfur Centered Reactive Intermediates in Chemistry and Biology (Chatgilialoglu, C., and Asmus, K. D., Eds.) pp 367-376, Plenum Press, New York.
    • (1990) Sulfur Centered Reactive Intermediates in Chemistry and Biology , pp. 367-376
    • Schöneich, C.1    Bonifacic, M.2    Dillinger, U.3    Asmus, K.D.4
  • 24
    • 0032978537 scopus 로고    scopus 로고
    • Phosphorecsence quenching method for measurement of intracellular pO2 in isolated skeletal muscle fibres
    • Hogan, M. C. (1999) Phosphorecsence quenching method for measurement of intracellular pO2 in isolated skeletal muscle fibres. J. Appl. Physiol. 86, 720-724.
    • (1999) J. Appl. Physiol. , vol.86 , pp. 720-724
    • Hogan, M.C.1
  • 25
    • 0035190320 scopus 로고    scopus 로고
    • Skeletal muscle intracellular pO2 assessed by myoglobin desaturation: Response to graded exercise
    • Richardson, R. S., Newcomer, S. C., and Noyszewski, E. A. (2001) Skeletal muscle intracellular pO2 assessed by myoglobin desaturation: Response to graded exercise. J. Appl. Physiol. 91, 2679-2685.
    • (2001) J. Appl. Physiol. , vol.91 , pp. 2679-2685
    • Richardson, R.S.1    Newcomer, S.C.2    Noyszewski, E.A.3
  • 26
    • 0034152767 scopus 로고    scopus 로고
    • Oxidative stress in bacteria and protein damage by reactive oxygen species
    • Cabiscol, E., Tamarit, J., and Ros, J. (2000) Oxidative stress in bacteria and protein damage by reactive oxygen species. Int. Microbiol. 3, 3-8.
    • (2000) Int. Microbiol. , vol.3 , pp. 3-8
    • Cabiscol, E.1    Tamarit, J.2    Ros, J.3
  • 27
    • 0000077349 scopus 로고
    • Pulse radiolytic investigations of peroxy radicals in aqueous solutions of acetate and glycine
    • Abramovitch, S. D., and Rabani, J. (1976) Pulse radiolytic investigations of peroxy radicals in aqueous solutions of acetate and glycine. J. Phys. Chem. 80, 1562-1565.
    • (1976) J. Phys. Chem. , vol.80 , pp. 1562-1565
    • Abramovitch, S.D.1    Rabani, J.2
  • 28
    • 0027293206 scopus 로고
    • Radical-induced chain oxidation of proteins and its inhibition by chain-breaking antioxidants
    • Neuzil, J., Gebicki, J. M., and Stocker, R. (1993) Radical-induced chain oxidation of proteins and its inhibition by chain-breaking antioxidants. Biochem. J. 293, 601-606.
    • (1993) Biochem. J. , vol.293 , pp. 601-606
    • Neuzil, J.1    Gebicki, J.M.2    Stocker, R.3
  • 29
    • 0031047884 scopus 로고    scopus 로고
    • Peroxy radical oxidation of thymidine
    • Martini, M., and Termini, J. (1997) Peroxy radical oxidation of thymidine. Chem. Res. Toxicol. 10, 234-241.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 234-241
    • Martini, M.1    Termini, J.2
  • 30
    • 0001712481 scopus 로고    scopus 로고
    • Significance of the intramolecular transformation of glutathione thiyl radicals to alpha-aminoalkyl radicals. Thermochemical and biological implications
    • Zhao, R., Lind, J., Merényi, G., and Eriksen, T. E. (1997) Significance of the intramolecular transformation of glutathione thiyl radicals to alpha-aminoalkyl radicals. Thermochemical and biological implications. J. Chem. Soc. Perkin Trans. 2 569-574.
    • (1997) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 569-574
    • Zhao, R.1    Lind, J.2    Merényi, G.3    Eriksen, T.E.4
  • 31
    • 0027183423 scopus 로고
    • Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalysed reactions
    • Stadtman, E. R. (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalysed reactions. Annu. Rev. Biochem. 62, 797-821.
    • (1993) Annu. Rev. Biochem. , vol.62 , pp. 797-821
    • Stadtman, E.R.1
  • 32
    • 0029002385 scopus 로고
    • Kinetic factors that control the fate of thiyl radicals in cells
    • Wardman, P., and von Sonntag, C. (1995) Kinetic factors that control the fate of thiyl radicals in cells. Methods Enzymol. 251, 31-45.
    • (1995) Methods Enzymol. , vol.251 , pp. 31-45
    • Wardman, P.1    Von Sonntag, C.2
  • 33
    • 0001065226 scopus 로고    scopus 로고
    • Rate constant determination for the reaction of hydroxyl and glutathione thiyl radicals with glutathione in aqueous solution
    • Mezyk, S. P. (1996) Rate constant determination for the reaction of hydroxyl and glutathione thiyl radicals with glutathione in aqueous solution. J. Phys. Chem. 100, 8861-8866.
    • (1996) J. Phys. Chem. , vol.100 , pp. 8861-8866
    • Mezyk, S.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.