Oxidation of cyclic dipeptides by photoinduced H-atom abstraction. A laser flash FT EPR and optical spectroscopy study

Journal of Physical Chemistry A

Volumn 111, Issue 23, 2007, Pages 4958-4964

  Tarábek, Peter ^a   Bonifačić, Marija ^b   Beckert, Dieter ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDANTS; PARAMAGNETIC RESONANCE;

CHEMICALLY INDUCED DYNAMIC ELECTRON POLARIZATION (CIDEP); CYCLIC DIPEPTIDES; HYDROGEN ABSTRACTION;

PEPTIDES;

CYCLOPEPTIDE; DIPEPTIDE; FREE RADICAL; HYDROGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; FOURIER ANALYSIS; LASER; LIGHT; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTOLYSIS; SPECTROSCOPY;

DIPEPTIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FOURIER ANALYSIS; FREE RADICALS; HYDROGEN; LASERS; LIGHT; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; PHOTOCHEMISTRY; PHOTOLYSIS; SPECTRUM ANALYSIS;

EID: 34347340517     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0709914     Document Type: Article

References (63)

1. Mee, L. K.; Adelstein, S. J. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2194-2198.
2. Gajewski, E.; Fuciarelli, A. F.; Dizdaroglu, M. Int. J. Radiat. Biol. 1988, 54, 445-459.
3. Dean, R. T.; Fu, S.; Stocker, R.; Davies, M. J. Biochem. J. 1997, 324, 1-18.
4. Wagner, A. F.; Frey, M.; Neugebauer, F. A.; Schafer, W.; Knappe, J. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 996-1000.
5. Burdi, D.; Aveline, B. M.; Wood, P. D.; Stubbe, J. A.; Redmond, R. W. J. Am. Chem. Soc. 1997, 119, 6457-6460.
6. Jonsson, M.; Wayner, D. D. M.; Armstrong, D. A.; Yu, D.; Rauk, A. J. Chem. Soc., Perkin Trans. 2 1998, 1967-1972.
7. Viehe, H. G.; Janousek, Z.; Merenyi, R.; Stella, L. Acc. Chem. Res. 1985, 18, 148-154.
8. Brocks, J. J.; Welle, F. M.; Beckhaus, H.-D.; Rüchardt, C. Tetrahedron Lett. 1997, 38, 7721-7724.
9. Reid, D. L.; Armstrong, D. A.; Rauk, A.; von Sonntag, C. Phys. Chem. Chem. Phys. 2003, 5, 3994-3999.
10. Rauk, A.; Yu, D.; Taylor, J.; Shustov, G. V.; Block, D. A.; Armstrong, D. A. Biochemistry 1999, 18, 9089-9096.
11. Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1998, 120, 8848-8855.
12. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744-2765.
13. Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1997, 119, 208-217.
14. Adams G. E.; Boag, J. W.; Currant, J.; Michael, B. D. Pulse Radiolysis; Academic Press: New York, 1965; pp 131-143.
15. Simic, M. G.; Neta, P.; Hayon, E. J. Am. Chem. Soc. 1970, 92, 4763-4768.
16. Rao, P. S.; Hayon, E. J. Phys. Chem. 1975, 79, 109-115.
17. Garrison, W. M. Chem. Rev. 1987, 87, 381-398.
18. Mieden, O. J.; von Sonntag, C. Z. Naturforsch. 1989, 44b, 959-974.
19. Paul, H.; Fischer, H. Helv. Chim. Acta 1971, 54, 485-491.
20. Livingston, R.; Doherty, D. G.; Zeldes, H. J. Am. Chem. Soc. 1975, 97, 3198-3204.
21. Rustgi, S. N.; Riesz, P. Int. J. Radiat. Biol. 1978, 34, 301-316.
22. Kland-English, M.; Garrison, W. M. Nature 1963, 197, 895-897.
23. Hayon, E.; Simic, M. J. Am. Chem. Soc. 1971, 93, 6781-6786.
24. Taniguchi, H.; Kirino, Y. J. Am. Chem. Soc. 1977, 99, 3625-3631.
25. Sevilla, M. D.; Fallor-Koszykowski, R. J. Phys. Chem. 1977, 81, 1198-1200.
26. Johns, R. B.; McGregor, J. W. Photochem. Photobiol. 1975, 22, 13-17.
27. Coyle, J. D.; Hill, R. R.; Randall, D. Photochem. Photobiol. 1984, 40, 153-159.
28. Edward, J. T. Research Corresp. 1955, 8, 38-39.
29. Bielinski, H.; Ciarkowski, J. Biopolymers 1986, 25, 795-809.
30. Sykes, B. D.; Robertson, E. B.; Dunford, H. B.; Konasewich, D. Biochemistry 1966, 5, 697-701.
31. Hakin, A. W.; Kowalchuck, M. G.; Liu, J. L.; Marriott, R. A. J. Solution Chem. 2000, 29, 131-151.
32. Hakin, A. W.; Liu, J. L.; O'Shea, M.; Zorzetti, B. Phys. Chem. Chem. Phys. 2003, 5, 2653-2657.
33. Prasad, C. Peptides 1995, 16, 151-164.
34. McCleland, K.; Milne, P. J.; Lucieto, F. R.; Frost, C.; Brauns, S. C.; Van, De Venter, M.; Du, Plesis, J.; Dyason, K. J. Pharm. Pharmacol. 2004, 56, 1143-1153.
35. Fdhila, F.; Vazquez, V.; Sanchez, J. L.; Riguera, R. J. Nat. Prod. 2003, 66, 1299-1301.
36. Mieden, O. J.; Schuchmann, M. N.; von Sonntag, C. J. Phys. Chem. 1993, 97, 3783-3790.
37. Mieden, O. J.; von Sonntag, C. J. Chem. Soc., Perkin Trans. 2 1989, 2071-2078.
38. Reid, D. L.; Armstrong, D. A.; Rauk, A.; Nese, C.; Schuchmann, M. N.; Westhoff, U.; von Sonntag, C. Phys. Chem. Chem. Phys. 2003, 5, 3278-3288.
39. Walling, C. Free Radicals in Solution; John Wiley and Sons, Inc.: New York, 1957.
40. Loeff, I.; Rabani, J.; Treinin, A.; Linschitz, H. J. Am. Chem. Soc. 1993, 115, 8933-8942.
41. Säuberlich, J.; Brede, O.; Beckert, D. J. Phys. Chem. A. 1997, 101, 5659-5665.
42. Kausche, T.; Sauberlich, J.; Trobitzsch, E.; Beckert, D.; Dinse, K. P. Chem. Phys. 1996, 208, 375-390.
43. Stephenson, D. S. Nucl. Magn. Reson. Spectrosc. 1988, 20, 515.
44. Säuberlich, J. Ph.D. Dissertation, University of Leipzig, 1996.
45. Geimer, J. Ph.D. Dissertation, University of Leipzig, 1999.
46. Kirino, Y.; Taniguchi, H. J. Am. Chem. Soc. 1976, 98, 5089-5096.
47. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637.
48. Neta, P.; Huie, R. E.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 1027-1284.
49. Huie, R. E.; Clifton, C. L. Int. J. Chem. Kinet. 1989, 21, 611-619.
50. NIST Standard Reference Database Number 69, June 2005 Release. http://webbook.nist.gov/chemistry/ie-ser.html, 2005.
51. Tarábek, P.; Bonifačić, M.; Beckert, D. J. Phys. Chem. A 2006, 110, 7293-7302.
52. Hayon, E.; Treinin, A.; Wilf, J. J. Am. Chem. Soc. 1972, 94, 47-57.
53. Geimer, J.; Beckert, D. Appl. Magn. Reson. 2000, 18, 505-513.
54. Kolthoff, I. M.; Miller, I. K. J. Am. Chem. Soc. 1951, 73, 3055-3059.
55. Tsao, M. S.; Wilmarth, W. K. J. Phys. Chem. 1959, 63, 346-353.
56. Dogliotti, L.; Hayon, E. J. Phys. Chem. 1967, 71, 2511-2516.
57. Chawla, O. P.; Fessenden, R. W. J. Phys. Chem. 1975, 79, 2693-2700.
58. Muus, L. T.; Atkins, P. W.; McLauchlan, K. A.; Pedersen, J. B. Chemically Induced Magnetic Polarization; D. Reidel Publishing Company: Dordrecht, 1977; pp 1-407.
59. McLauchlan, K. A.; Simpson, N. J. K.; Smith, P. D. Res. Chem. Intermed. 1991, 16, 141-163.
60. McLauchlan, K. A. In Continuous-Wave Transient Electron Spin Resonance, Modern Pulsed and Continuous-Wave Electron Spin Resonance; Kevan, L., Bowman, M. K., Eds.; John Wiley and Sons, Inc.: New York, 1990; pp 285-364.
61. McLauchlan K. A.; Yeung, M. T. Time-Resolved ESR Studies of Free Radicals, Specialist Periodical Reports, Electron Spin Resonance, Vol. 14; The Royal Society of Chemistry: Cambridge, U.K., 1994; pp 32-62.
62. Verma, N. C.; Fessenden, R. W. J. Chem. Phys. 1976, 65, 2139-2155.
63. Woodward, J. R.; Lin, T. S.; Sakaguchi, Y.; Hayashi, H. J. Phys. Chem. A 2000, 104, 557-561.