3-Hydroxylysine, a potential marker for studying radical-induced protein oxidation

Chemical Research in Toxicology

Volumn 11, Issue 11, 1998, Pages 1265-1273

  Morin, Éédicte ^a   Bubb, William A ^b   Davies, Michael J ^a   Dean, Roger T ^a   Fu, Shanlin ^a  

^a HEART RESEARCH INSTITUTE   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLYSINE;

AMINO ACID ANALYSIS; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PROTEIN DEGRADATION; PROTEIN DETERMINATION; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

AMINO ACIDS; ANIMALS; BIOLOGICAL MARKERS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORENES; FREE RADICALS; GAMMA RAYS; HUMANS; HYDROXYLYSINE; MASS SPECTROMETRY; OXIDATION-REDUCTION; PEPTIDES; PROTEINS; SOLVENTS;

EID: 3643103075     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980118h     Document Type: Article

References (33)

1. Gebicki, S., and Gebicki, J. M. (1993) Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem. J. 289, 743-749.
2. Simpson, J. A., Narita, S., Gieseg, S., Gebicki, S., Gebicki, J. M., and Dean, R. T. (1992) Long-lived reactive species on free-radicaldamaged proteins. Biochem. J. 282, 621-624.
3. Stadtman, E. R. (1992) Protein oxidation and aging. Science 257, 1220-1224.
4. Oliver, C. N., Ahn, B. W., Moerman, E. J., Goldstein, S., and Stadtman, E. R. (1987) Age-related changes in oxidized proteins. J. Biol. Chem. 262, 5488-5491.
5. Garrison, W. M. (1987) Reaction mechanisms in the radiolysis of peptides, polypeptides, and proteins. Chem. Rev. 87, 381-398.
6. Fu, S., Hick, L. A., Sheil, M. M., and Dean, R. T. (1995) Structural identification of valine hydroperoxides and hydroxides on radicaldamaged amino acid, peptide, and protein molecules. Free Radical Biol. Med. 19, 281-292.
7. Davies, M. J., and Dean, R. T. (1997) Radical-mediated protein oxidation: from chemistry to medicine, pp 1-443, Oxford University Press, Oxford, U.K.
8. Dean, R. T., Fu, S., Stocker, R., and Davies, M. J. (1997) The biochemistry and pathology of radical-mediated protein oxidation. Biochem. J. 324, 1-18.
9. Fu, S., and Dean, R. T. (1997) Structural characterisation of the products of hydroxyl radical damage to leucine and their detection on proteins. Biochem. J. 324, 41-48.
10. Fu, S., Fu, M. X., Baynes, J. W., Thorpe, S. R., and Dean, R. T. (1998) Presence of DOPA and amino acid hydroperoxides in proteins modified with advanced glycation end products (AGEs): amino acid oxidation products as a possible source of oxidative stress induced by AGE proteins. Biochem. J. 330, 233-239.
11. Fu, S., Davies, M. J., Stocker, R., and Dean, R. T. (1998) Evidence for roles of radicals in protein oxidation in advanced human atherosclerotic plaque. Biochem. J. 333, 519-525.
12. Ayala, A., and Cutler, R. G. (1996) The utilization of 5-hydroxyl-2-amino valeric acid as a specific marker of oxidised arginine and proline residues in proteins. Free Radical Biol. Med. 21, 65-80.
13. Davies, M. J., Fu, S., and Dean, R. T. (1995) Protein hydroperoxides can give rise to reactive free radicals. Biochem. J. 305, 643-649.
14. Davies, M. J. (1996) Protein and peptide alkoxyl radicals can give rise to C-terminal decarboxylation and backbone cleavage. Arch. Biochem. Biophys. 336, 163-172.
15. Trelstad, R., Lawley, L. R., and Holmes, L. B. (1981) Nonenzymatic hydroxylations of proline and lysine by reduced oxygen derivatives. Nature 289, 310-312.
16. Jessup, W., Dean, R. T., and Gebicki, J. M. (1994) Iodometric determination of hydroperoxides in lipids and proteins. Methods Enzymol. 233, 289-303.
17. Einarsson, S., Josefsson, B., and Lagerkvist, S. (1983) Determination of amino acids with 9-fluorenylmethylchloroformate and reverse-phase high-performance liquid chromatography. J. Chromatogr. 282, 609-618.
18. Lewis, J. R. E., Morley, J. S., and Venn, R. F. (1993) Analysis of human β-endorphin 28-31 (melanotropin potentiating factor) and analogues by high-performance liquid chromatography of their 9-fluorenylmethoxy-carbonyl derivatives. J. Chromatogr. 615, 3745.
19. Chen, R. F., Scott, C., and Trepman, E. (1979) Fluorescence properties of o-phthaldialdehyde derivatives of amino acids. Biochim. Biophys. Acta 576, 440-455.
20. Fu, S., Gebicki, S., Jessup, W., Gebicki, J. M., and Dean, R. T. (1995) Biological fate of amino acid, peptide and protein hydroperoxides. Biochem. J. 311, 821-827.
21. Jackman, L. M., and Sternhell, S. (1969) Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, pp 1-163, Pergamon Press, Oxford, U.K.
22. Kalinowski, H. O., Berger, S., and Braun, S. (1994) Carbon-13 NMR Spectroscopy, pp 1-179, Wiley, Chichester, U.K.
23. Hughes, P. F., Smith, S. H., and Olson, J. T. (1994) Two chiral syntheses of threo-3-Hydroxylysine. J. Org. Chem. 59, 5799-5802.
24. Gebicki, J. M., and Guille, J. (1989) Spectrophotometric and high performance Chromatographic assays of hydroperoxides by iodometric technique. Anal. Biochem. 176, 360-364.
25. Stadtman, E. R. (1990) Covalent modification reactions are marking steps in protein turnover. Biochemistry 29, 6323-6331.
26. Stadtman, E. R. (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62, 797-821.
27. Levine, R. L. (1984) Mixed-function oxidation of histidine residues. Methods Enzymol. 107, 370-376.
28. Russell, G. A. (1957) Deuterium-isotope effects in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals. J. Am. Chem. Soc. 79, 3871-3877.
29. von Sonntag, C. (1987) The chemical basis of radiation biology, pp 1-515, Taylor and Francis, London.
30. Hawkins, C. L., and Davies, M. J. (1997) Oxidative damage to collagen and related substrates by metal ion/hydrogen peroxide systems: random attack or site-specific damage? Biochim. Biophys. Acta 1360, 84-96.
31. - and OH radicals with simple peptides in aqueous solution. Optical absorption spectra of intermediates. J. Am. Chem. Soc. 92, 4763-4768.
32. Rao, P. S., and Hayon, E. (1975) Reactions of hydroxyl radicals with oligopeptides in aqueous solutions. J. Phys. Chem. 79, 109-115.
33. -) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513-886.