Toward site specificity of oxidative damage in proteins: C-H and C-C bond dissociation energies and reduction potentials of the radicals of alanine, serine, and threonine residues - An ab initio study

Journal of the American Chemical Society

Volumn 119, Issue 1, 1997, Pages 208-217

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

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CALCULATION; COMPUTER SIMULATION; MOLECULAR DYNAMICS; OXIDATION; PROTEIN DEGRADATION; PROTEIN STRUCTURE; REACTION ANALYSIS; THEORY;

EID: 0031042252     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9618210     Document Type: Article

References (53)

1. Stadman, E. R. Anna. Rev. Biochem. 1993, 62, 797.
2. Sies, H. Oxygen Stress; Academic Press: London, 1985.
3. Sies, H. Oxidative Stress-Oxidants and Anti-Oxidants; Academic Press: London, 1991.
4. Simic, M. G.; Taylor, K. A.; Ward, J. F.; von Sonntag, C. Oxygen Radicals in Biology and Medicine; Plenum Press: New York, 1988.
5. Davies, K. J. A. Oxidative Damage and Repair: Chemical, Biological and Medical Aspects; Pergamon Press: New York, 1991.
6. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987.
7. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513.
8. Sharpatyi, V. A. High Energy Chem. 1995, 29, 85.
9. Garrison, W. M. Curr. Top. Radiat. Res. 1968, 4, 43; Radial. Res. Rev. 1972, 3, 305.
10. Garrison, W. M. Curr. Top. Radiat. Res. 1968, 4, 43; Radial. Res. Rev. 1972, 3, 305.
11. Mieden, O. J.; von Sonntag, C. Z. Naturforsch. 1989, 44b, 959.
12. Mieden, O. J.; Schuchmann, M. N.; von Sonntag, C. J. Phys. Chem. 1993, 97, 3783.
13. von Sonntag, C.; Schuchmann, H.-P. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; NATO ASI Series; Plenum Press: New York, 1990; p 409,
14. Wardman, P. In Atmospheric Oxidation and Antioxidants; Scott, G., Ed.; Elsevier: New York, 1993; Vol. 3, p 101.
15. Wardman, P.; Von Sonntag, C. Methods Enzymol. 1995, 251, 31.
16. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637.
17. Faraggi, M.; Klapper, M. H. J. Chim. Phys. 1993, 90, 711.
18. Armstrong, D. A.; Rauk, A.; Yu, D. J. Chem. Soc., Perkin Trans. 2 1995, 553.
19. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. J. Am. Chem. Soc. 1994, 116, 12010.
20. Armstrong, D. A., Rauk, A.; Yu, D. Can. J. Chem. 1996, 74, 1192.
21. Leroy, G.; Sana, M.; Wilante, C. J. Mol. Struct, 1991, 228, 37.
22. Hehre, W. J.: Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1970, 92, 4796.
23. Yu, D.; Armstrong, D. A; Rauk, A. Can. J. Chem. 1992, 70, 1762.
24. Yu, D.; Rauk, A.; Armstrong, D, A. J. Am. Chem. Soc. 1995, 117, 1789.
25. Barone, V.; Adamo, C.; Grand, A.; Brunei, Y.; Fontecave, M.; Subra, R. J. Am. Chem. Soc. 1995, 117, 1083.
26. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision B; Gaussian, Inc.: Pittsburgh, PA, 1992.
27. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart. J. P.; Headr-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, SGI Revision B.3; Gaussian, Inc.: Pittsburgh, PA. 1995.
28. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
29. McQuarrie, D. A. Statistical thermodynamics; Harper & Row: New York, 1973.
30. Wagman, D. D.; Evans, W. H.; Parker, V. B.; Schumm, R, H.; Halow, I.; Bailey, S. M.; Chumey, K. L.; Nuttal, R. L. J. Phys. Chem. Ref. Data 1982, 11 (Suppl. 2).
31. Kanabus-Kaminska, J. M.; Gilbert, B. C; Griller, D. J. Am. Chem. Soc. 1989, 111, 3311.
32. See ref 15, p 1644, for derivation.
33. -1.
34. O'Hair, R. A. J.; Bowie, J. H.; Gronert, S. Int. J. Mass Ion Proc. 1992, 117,23.
35. Gronert, S.; O'Hair, R. A. J. J. Am. Chem. Soc. 1995, 117, 2071.
36. Csaszar, A. G. J. Phys. Chem. 1996, 100, 3541.
37. Ciesielski, B.; Wielopolski, L. Radiat. Res. 1994, 140, 105.
38. van Alsenoy, C.; Scarsdale, J. N.; Sellers, H. L.; Schafer, L. Chem. Phys. Lett. 1981, 80, 124.
39. van Alsenoy, C.; Kulp, S.; Siam, K.; Klimkowski, V. J.; Ewbank, J. D.; Schafer, L. J. Mol. Struct. 1988, 181, 169.
40. Schafer, L.; Kulp-Newton, S. Q.; Siam, K.; Klimkowski, V. J.; van Alsenoy, C. J. Mol. Struct. 1990, 209, 373.
41. CH are obtained from the earlier data of: McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
42. CH are obtained from the earlier data of: McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
43. (a) Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1986, 90, 5915.
44. (b) Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1987, 91, 6532.
45. Griller, D.; Simões, J. A. M.; Wayner, D. D. M. Thermochemistry of Sulfur-Centered Intermediates. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; NATO ASI Series; Plenum Press: New York, 1990; pp 37-52.
46. Actually it should be noted that for true repair to occur maintenance of the stereochemistry is mandatory. Akhlaq, M. S.; Schuchmann, H.-P.; von Sonntag, C. Int. J. Radiat. Biol. 1987, 51, 91.
47. Eriksen, T. E.; Fransson, G. Radiat. Phys. Chem. 1988, 32, 163
48. Grierson, L.; Hildenbrand, K.; Bothe, E. Int. J. Radiat. Biol. 1992, 62, 265.
49. Merényi, G.; Lind, J.; Engman, L. J. Chem. Soc., Perkin Trans. 2 1994, 2551.
50. Lind, J.; Shen, X.; Ericksen, T.; Merényi, G. J. Am. Chem. Soc. 1990, 112, 479.
51. Ngauv, S. N.; Sabbah, R.; Lafette, M. Thermochim. Acta 1977, 20, 371.
52. de Kruif, C. G.; Voogd, J.; Offringa, J. C. A. J. Chem. Thermodyn. 1979, 11, 651.
53. Corrected using gas phase heat capacity data from the present ab initio results and solid phase experimental data from: Hutchens, T. O.; Cole, A. G.; Stout, J. W. J. Am. Chem. Soc. 1960, 82, 4813,