Oxidative damage to the glycyl α-carbon site in proteins: An ab initio study of the C-H bond dissociation energy and the reduction potential of the C-centered radical

Canadian Journal of Chemistry

Volumn 74, Issue 6, 1996, Pages 1192-1199

  Armstrong, D A ^a   Yu, D ^a   Rauk, A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

ab initio; amino acid; bond energy; computation; glycine; peptide; radicals

Indexed keywords

AMINO ACIDS; CALCULATIONS; CHEMICAL REACTIONS; MOLECULES; OXIDATION; PROTEINS;

BOND DISSOCIATION ENERGY; GLYCYLCARBON SITE; ISODESMIC REACTIONS; OXIDATIVE DAMAGE; REDUCTION POTENTIAL;

CHEMICAL BONDS;

GLYCINE; GLYCINE DERIVATIVE;

ARTICLE; CALCULATION; COMPUTER SIMULATION; PROTEIN DEGRADATION; STRUCTURE ACTIVITY RELATION; THEORY;

EID: 0030175259     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-134     Document Type: Article

References (39)

1. E.R. Stadman. Annu. Rev. Biochem. 62, 797 (1993).
2. R.T. Dean. In Oxidative damage and repair: chemical, biological and medical aspects. Edited by K.J.A. Davies. Pergamon Press, New York. 1991. pp. 341-347.
3. W.M. Garrison. Radiat. Res. Rev. 3, 305 (1972).
4. H. Sies. In Oxygen stress. Academic Press, London. 1985.
5. M.G. Simic, K.A. Taylor, J.F. Ward, and C. von Sonntag. Oxygen radicals in biology and medicine. Plenum Press, New York. 1988.
6. H. Sies. In Oxidative stress - oxidants and anti-oxidants. Academic Press, London. 1991.
7. K.J.A. Davies. Oxidative damage and repair: chemical, biological and medical aspects. Pergamon Press, New York. 1991.
8. C. von Sonntag. The chemical basis of radiation biology. Taylor and Francis, London. 1987.
9. O.J. Mieden and C. von Sonntag. Z. Naturforsch. B: Chem. Sci. 44, 959 (1989).
10. L. Grierson, K. Hildenbrand, and E. Bothe. Int. J. Radiat. Biol. 62, 265 (1992).
11. P. Wardman. In Atmospheric oxidation and antoxidants. Vol. III. Edited by G. Scott. Elsevier, Amsterdam. 1993. pp. 101-127.
12. D. Griller, J.A.M. Simões, and D.D.M. Wayner. In Sulfur-centered reactive intermediates in chemistry and biology. Edited by C. Chatgilialoglu and K.-D. Asmus. NATO ASI Ser. Plenum Press, New York. 1990. pp. 37-52.
13. D.F. McMillen and D.M. Golden. Annu. Rev. Phys. Chem. 33, 493 (1982).
14. R. Zhao, J. Lind, G. Merényi, and T. Eriksen. J. Am. Chem. Soc. 116, 12010 (1994).
15. X. Zhang, N. Zhang, H.-P. Schuchmann, and C. von Sonntag. J. Phys. Chem. 98, 6541 (1994).
16. G. Leroy, M. Sana, and C. Wilante. J. Mol. Struct. 228, 37 (1991).
17. F.G. Bordwell, X.-M. Zhang, and M.S. Alnajjar. J. Am. Chem. Soc. 114, 7623 (1992).
18. H.-G. Viehe, Z. Janousek, R. Merényi, and L. Stella. Acc. Chem. Res. 18, 148 (1985).
19. R. Sustman and H.-G. Korth. Adv. Phys. Org. Chem. 26, 131 (1990).
20. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, and J.A. Pople. Gaussian 92, Revision B. Gaussian, Inc., Pittsburgh, Pa. 1992.
21. D. Yu, A. Rauk, and D.A. Armstrong. J. Chem. Soc. Perkin Trans. 2, 2207 (1994).
22. D. Yu, D.A. Armstrong, and A. Rauk. Can. J. Chem. 70, 1762 (1992).
23. D. Yu, A. Rauk, and D.A. Armstrong. J. Am. Chem. Soc. 117, 1789 (1995).
24. D.A. Armstrong, A. Rauk, and D. Yu. J. Chem. Soc. Perkin Trans. 2, 553 (1995).
25. L.A. Curtiss, K. Raghavachari, and J.A. Pople. J. Chem. Phys. 98, 1293 (1993).
26. W.J. Hehre, R. Ditchfield, L. Radom, and J.A. Pople. J. Am. Chem. Soc. 92, 4796 (1970).
27. D.A. McQuarrie. Statistical thermodynamics. Harper & Row, New York. 1973.
28. S.G. Lias, J.E. Bartmess, J.F. Liebman, J.L. Holmes, R.D. Levin, and W.G. Mallard. J. Phys. Chem. Ref. Data, 17, Suppl. No. 1 (1988).
29. V.M. Orlov, A.D. Misharev, V.V. Takhistov, and I.I. Ryabinkin. Izv. Akad. Nauk SSSR, Ser. Khim. 7, 1514 (1988).
30. A. Perczel, M.A. McAllister, P. Császàr, and I.G. Csizmadia. Can. J. Chem. 72, 2050 (1994).
31. F.C. Bernstein, T.F. Koetzle, G.J.B. Williams, E.F. Meyer, Jr., M.D. Brice, Jr., J.R. Rodgers, O. Kennard, T. Shimanouchi, and M. Tasumi. J. Mol. Biol. 112, 535 (1977).
32. W. Traub. In Peptides, polypeptides and proteins. Edited by E.R. Blout, F.A. Bovey, M. Goodman, and N. Lotan. John Wiley and Sons, New York. 1974. p. 146.
33. S.A. Fossey, G. Nemethy, K.D. Gibson, and H.A. Scheraga. Biopolymers, 31, 1529 (1991).
34. D.D. Wagman, W.H. Evans, V.B. Parker, R.H. Schumm, I. Holow, S.M. Bailey, K.L. Churney, and R.L. Nuttal. J. Phys. Chem. Ref. Data, 11, Suppl. No. 2 (1982).
35. P.S. Surdhar and D.A. Armstrong. J. Phys. Chem. 90, 5915 (1986).
36. P.S. Surdhar and D.A. Armstrong. J. Phys. Chem. 91, 6532 (1987).
37. G. Merényi, J. Lind, and L. Engman. J. Chem. Soc. Perkin Trans. 2, 2551 (1994).
38. M. Faraggi and M.H. Klapper. Chim. Phys. 90, 711 (1993).
39. P. Wardman. J. Phys. Chem. Ref. Data, 18, 1637 (1989).