Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize α-amino acids to a family of reactive aldehydes: Mechanistic studies identifying labile intermediates along the reaction pathway

Journal of Biological Chemistry

Volumn 273, Issue 9, 1998, Pages 4997-5005

  Hazen, Stanley L ^a,c   D'Avignon, Andre ^b   Anderson, Melissa M ^a   Hsu, Fong F ^a   Heinecke, Jay W ^b,d,e  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY   (United States)

^c LERNER RESEARCH INSTITUTE   (United States)

^d AMERICAN HEART ASSOCIATION   (United States)

^e Box 8046   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALPHA AMINO ACID; CHLORIDE; HYDROGEN PEROXIDE; MYELOPEROXIDASE;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IONIZING RADIATION; MASS SPECTROMETRY; NEUTROPHIL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ALDEHYDES; AMINO ACIDS; CHLORAMINES; CHLORIDES; HUMANS; HYPOCHLOROUS ACID; LYSINE; MASS SPECTROMETRY; MODELS, CHEMICAL; NEUTROPHILS; NITROGEN ISOTOPES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PEROXIDASE; PHENYLALANINE; TYROSINE;

EID: 0032570808     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.273.9.4997     Document Type: Article

References (42)

1. Klebanoff, S. J., and Clark, R. A. (1978) The Neutrophil: Function and Clinical Disorders, pp. 447-451, Elsevier/North Holland Biomedical Press, Amsterdam
2. Babior, B. M., Kipnes, R. S., and Curnutte, J. T. (1973) J. Clin. Invest. 52, 741-744
3. Hazen, S. L., Hsu, F. F., d'Avignon, A., and Heinecke, J. W. (1998) Biochemistry, in press
4. Sharpless, N. E., Blair, A. E., and Maxwell, C. R. (1955) Radiat. Res. 2, 135-144
5. Maxwell, C. R., Paterson, D. C., and White, C. (1955) Radiat. Res. 2, 431-438
6. Swallow, A. J. (1960) Radiation Chemistry of Organic Compounds, pp. 200-224, Pergamon Press Inc., Tarrytown, NY
7. Garrison, W. M. (1964) Radiat. Res. 4, (suppl.) 158-170
8. Garrison, W. M. (1968) Curr. Top. Radiat. Res. 4, 43-94
9. Stadtman, E. R. (1993) Annu. Rev. Biochem. 62, 797-821
10. Stadtman, E. R., and Berlett, B. S. (1991) Prof. Natl. Acad. Sci. U. S. A. 87, 389-393
11. Dakin, H. D. (1905) J. Biol. Chem. 1, 171-176
12. Dakin, H. D. (1908) J. Biol. Chem. 4, 63-76
13. Dakin, H. D. (1908) J. Biol. Chem. 5, 409-411
14. Harrison, J. E., and Schultz, J. (1976) J. Biol. Chem. 251, 1371-1374
15. Weiss, S. J., Klein, R., Slivka, A., and Wei, M. (1982) J. Clin. Invest. 70, 598-607
16. Kettle, A. J., and Winterbourn, C. C. (1994) Methods Enzymol. 233, 502-512
17. Thomas, E. L., Grisham, M. B., and Jefferson, M. M. (1986) Methods Enzymol. 132, 569-585
18. Zgliczynski, J. M., Stelmaszynska, T., Domanski, J., and Ostrowski, W. (1971) Biochim. Biophys. Acta 235, 419-424
19. Albrich, J., McCarthy, C., and Hurst, J. (1982) Proc. Natl. Acad. Sci. U. S. A. 78, 210-214
20. Weiss, S. J., Lampert, M. B., and Test, S. T. (1983) Science 222, 625-628
21. Grisham, M. B., Jefferson, M. M., and Thomas, E. L. (1984) J. Biol. Chem. 259, 6757-6765
22. Test, S. T., Lampert, M. B., Ossanna, P. J., Thoene, J. G., and Weiss, S. J. (1984) J. Clin. Invest. 74, 1341-1349
23. Thomas, E. L., Grisham, M. B. Melton, D. F., and Jefferson, M. M. (1985) J. Biol. Chem. 260, 3321-3329
24. Linder, M., (1992) Nutritional Biochemistry and Metabolism, p. 98, Elsevier Science Publishing Co., Inc., New York
25. Monnier, V. M., Sell, D. R., Nagaraj, R. H., and Miyata, S. (1991) Gerontology 37, 152-165
26. Anderson, M. M., Hazen, S. L., Hsu, F. F., and Heinecke, J. W. (1997) J. Clin. Invest. 99, 424-432
27. Rowbottom, J. (1955) J. Biol. Chem. 212, 877-885
28. Raper (1932) Biochem. J. 26, 2000-2094
29. Knapp, D. R. (1979) Handbook of Analytical Derivatization Reactions, pp. 485-486, John Wiley & Sons, Inc., New York
30. Shriner, R. L., Fuson, R. C., Curtin, D. Y., and Morrill, T. C. (1980) The Systematic Identification of Organic Compounds: A Laboratory Manual, 6th Ed., pp. 161-184, John Wiley & Sons, Inc., New York
31. Furukawa, J., and Saegusa, T. (1963) Polymerization of Aldehydes and Oximes, pp. 43-123, Interscience Publishers of John Wiley & Sons, Inc., New York
32. Schauenstein E., and Esterbauer, H. (1978) CIBA Found. Symp. 67, 225-44
33. Weiss, S. J., Test, S. T., Eckman, C. M., Ross, D., and Regiani, S. (1986) Science 234, 200-203
34. Hazen, S. L., Gaut, J. P., Hsu, F. F., Crowley, J. R., d'Avignon, A., and Heinecke, J. W. (1997) J. Biol. Chem. 272, 16990-16998
35. Mayeno, A. N., Curran, A. J., Roberts, R. L., and Foote, C. S. (1989) J. Biol. Chem. 264, 5660-5668
36. Thomas, E. L., Bozeman, P. M., Jefferson, M. M., and King, C. C. (1995) J. Biol. Chem. 270, 2906-2913
37. Bass, D. A. (1985) in Cecil Textbook of Medicine (Wyngaarden, J. B., and Smith, L. H., eds) pp. 1011-1013, W. B. Saunders Co., Philadelphia
38. Palinski, W., Ord, V., Plump, A. S., Breslow, J. L., Steinberg, D., and Witztum, J. L. (1994) Arterioscler. Thromb. 14, 605-616
39. Palinski, W., Horkko, S., Miller, E., Steinbrecher, U. P., Powell, H. C., Curtiss, L. K., and Witztum, J. L. (1996) J. Clin. Invest. 98, 800-814
40. Steinbrecher, U. P., and Lougheed, M. (1992) Arterioscler. Thromb. 12, 608-625
41. Daugherty, A., Dunn, J. L., Rateri, D. L., and Heinecke, J. W. (1994) J. Clin. Invest. 94, 437-444
42. Hazen, S. L., and Heinecke, J. W. (1997) J. Clin. Invest. 99, 2075-2081.