Photooxidation of Methionine Derivatives by the 4-Carboxybenzophenone Triplet State in Aqueous Solution. Intracomplex Proton Transfer Involving the Amino Group

Photochemistry and Photobiology

Volumn 68, Issue 6, 1998, Pages 785-796

  Hug, Gordon L ^a   Bobrowski, Krzysztof ^a,b   Kozubek, Halina ^c   Marciniak, Bronislaw ^a,c  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b INSTITUTE OF NUCLEAR CHEMISTRY AND TECHNOLOGY   (Poland)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000854708     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb05285.x     Document Type: Article

References (52)

1. Chatgilialoglu, C. and K.-D. Asmus (1990) Sulfur-Centered Reactive Intermediates in Chemistry and Biology, Vol. 197. NATO ASI Series, Series A: Life Sciences, Plenum Press, New York.
2. Asmus, K.-D. and M. Bonifacic (1994) Free radical chemistry. In Exercise and Oxygen Toxicity (Edited by C. K. Sen, L. Packer and O. Hanninen), pp. 1-47. Elsevier, Amsterdam.
3. Bonifacic, M., H. Möckel, D. Bahnemann and K.-D. Asmus (1975) Formation of positive ions and other primary species in the oxidation of sulphides by hydroxyl radicals. J. Chem. Soc. Perkin Trans. 2, 675-685.
4. Schöneich, C. and K. Bobrowski (1993) Intramolecular hydrogen transfer as the key step in the dissociation of hydroxyl radical adducts of (alkylthio)ethanol derivatives. J. Am. Chem. Soc. 115, 6538-6547.
5. Guttenplan, J. B. and S. G Cohen (1973) Quenching and reduction of photoexcited benzophenone by thioethers and mercaptans. J. Org. Chem. 38, 2001-2007.
6. Bobrowski, K., B. Marciniak and G. L. Hug (1994) A reinvestigation of the mechanism of photoreduction of benzophenones by alkyl sulfides. J. Photochem. Photobiol. A 81, 159-168.
7. Marciniak, B., K. Bobrowski, G. L. Hug and J. Rozwadowski (1994) Photoinduced electron transfer between sulfur-containing carboxylic acids and the 4-carboxybenzophenone triplet state in aqueous solution. J. Phys. Chem. 98, 4854-4860.
8. Cohen, S. G. and S. Ojanpera (1975) Photooxidation of methionine and related compounds. J. Am. Chem. Soc. 97, 5633-5634.
9. Bobrowski, K., B. Marciniak and G. L. Hug (1992) 4-Carboxybenzophenone-sensitized photooxidation of sulfur-containing amino acids. Nanosecond laser flash photolysis and pulse radiolysis studies. J. Am. Chem. Soc. 114, 10279-10288.
10. Bobrowski, K., G. L. Hug, B. Marciniak and H. Kozubek (1994) 4-Carboxybenzophenone-sensitized photooxidation of sulfur-containing amino acids in alkaline aqueous solutions. Secondary photoreactions kinetics. J. Phys. Chem. 98, 537-544.
11. Marciniak, B., G. L. Hug, K. Bobrowski and H. Kozubek (1995) Mechanism of 4-carboxybenzophenone-sensitized photooxidation of methionine-containing dipeptides and tripeptides in aqueous solution. J. Phys. Chem. 99, 13560-13568.
12. Bobrowski, K., G. L. Hug, B. Marciniak, B. L. Miller and C. Schöneich (1997) Mechanism of one-electron oxidation of β-, γ-, and δ-hydroxyalkyl sulfides. Catalysis through intramolecular proton transfer and sulfur-oxygen bond formation. J. Am. Chem. Soc. 119, 8000-8011.
13. Cilento, G. (1982) Electronic excitation in dark biological processes. In Chemical and Biological Generation of Excited States (Edited by W. Adam and G. Cilento), pp. 277-307. Academic Press, New York.
14. Cilento, G. (1984) Generation of electronically excited triplet species in biological systems. Pure Appl. Chem. 56, 1179-1190.
15. Cohen, S. G., A. Parola and G. H. Parsons, Jr. (1973) Photoreduction by amines. Chem. Rev. 73, 141-161.
16. Shaefer, C. G. and K. S. Peters (1980) Picosecond dynamics of the photoreduction of benzophenone by triethylamine. J. Am. Chem. Soc. 102, 7566-7567.
17. Lewis, F. D. (1979) Formation and reactions of stilbene exciplexes. Acc. Chem. Res. 12, 152-158.
18. Das, S. and C. von Sonntag (1986) The oxidation of trimethylamine by OH radicals in aqueous solution, as studied by pulse radiolysis, ESR, and product analysis. The reactions of the alkylamine radical cation, the aminoalkyl radical, and the protonated aminoalkyl radical. Z. Naturforsch. B Anorg. Chem. Org. Chem. 41B, 505-513.
19. Xu, W., X.-M. Zhang and P. S. Mariano (1991) Single electron transfer promoted photocyclization reactions of (aminoalkyl)cyclohexenones. Mechanistic and synthetic features of processes involving the generation and reactions of amine cation and α-amino radicals. J. Am. Chem. Soc. 113, 8863-8878.
20. Mönig, J., R. Goslich and K.-D. Asmus (1986) Thermodynamics of S∴S 2σ/1σ* three-electron bonds and deprotonation kinetics of thioether radical cations in aqueous solution. Ber. Bunsen-ges. Phys. Chem. 90, 115-121.
21. Asmus, K.-D., M. Göbl, K.-O. Hiller, S. Mahling and J. Mönig (1985) S∴N and S-O three-electron-bonded radicals and radical cations in aqueous solutions. J. Chem. Soc. Perkin Trans. 2, 641-646.
22. .OH radical induced decarboxylation of amino acids. Decarboxylation vs bond formation in radical intermediates. J. Am. Chem. Soc. 113, 2141-2145.
23. .OH radical induced decarboxylation of methionine-containing peptides. Influence of peptide sequence and net charge. J. Chem. Soc. Perkin Trans. 2, 353-362.
24. .OH radical induced decarboxylation of γ-glutamylmethionine and S-alkylglutathione derivatives: evidence for two different pathways involving C- and N-terminal decarboxylation. J. Chem. Soc. Perkin Trans. 2, 975-980.
25. Hug, G. L., B. Marciniak and K. Bobrowski (1996) Sensitized photo-oxidation of sulfur-containing amino acids and peptides in aqueous solution. J. Photochem. Photobiol. A 95, 81-88.
26. Encinas, M. V. and J. C. Scaiano (1979) Electron transfer processes in the photochemistry of β-(dimethylamino)propiophenone. J. Am. Chem. Soc. 101, 2146-2152.
27. - with X = Cl, Br, I, and SCN. J. Phys. Chem. 89, 2330-2335.
28. Christie, J. H., J. A. Turner and R. A. Osteryoung (1977) Square wave voltammetry at the dropping mercury electrode: theory. Anal. Chem. 49, 1899-1903.
29. 2O-saturated solutions. J. Phys. Chem. 86, 2078-2084.
30. Schuler, R. H. (1985) Computerised instrumentation in chemical experiments. Chem. Educ. 2, 34-37.
31. Marciniak, B., K. Bobrowski and G. L. Hug (1993) Quenching of triplet states of aromatic ketones by sulfur-containing amino acids in solution. Evidence for electron transfer. J. Phys. Chem. 97, 11937-11943.
32. Schöneich, C., F. Zhao, K. P. Madden and K. Bobrowski (1994) Side chain fragmentation of N-terminal threonine or serine residue induced through intramolecular proton transfer to hydroxy sulfuranyl radical formed at neighboring methionine in dipeptides. J. Am. Chem. Soc. 116, 4641-4652.
33. Bevington, P. R. (1969) Data Reduction and Error Analysis for the Physical Sciences. McGraw-Hill, New York.
34. + radical cation. J. Phys. Chem. 100, 14914-14921.
35. Inbar, S., H. Linschitz and S. G. Cohen (1981) Quenching, radical formation, and disproportionation in the photoreduction of 4-carboxybenzophenone by 4-carboxybenzhydrol, hydrazine, and hydrazinium ion. J. Am. Chem. Soc. 103, 7323-7328.
36. Hurley, J. K., H. Linschitz and A. Treinin (1988) Interaction of halide and pseudohalide ions with triplet benzophenone-4-carboxylate: kinetics and radical yields. J. Phys. Chem. 92, 5151-5159.
37. Pogocki, D. M. (1996) Investigation of radical processes induced by hydroxyl radical in amino acids and peptides containing thioether group. Ph.D. thesis, Department of Radiation Chemistry and Technology, Institute of Nuclear Chemistry and Technology, Warsaw, Poland.
38. 2O-saturated aqueous solutions. J. Phys. Chem. 85, 192-199.
39. . radical induced oxidation of methionine in aqueous solution. J. Am. Chem. Soc. 103, 2734-2743.
40. Lutz, H., E. Breheret and L. Lindqvist (1973) Effects of solvent and substituents on the absorption spectra of triplet acetophenone and the acetophenone ketyl radical studied by nanosecond laser photolysis. J. Phys. Chem. 77, 1758-1762.
41. Carmichael, I. and G. L. Hug (1986) Triplet-triplet absorption spectra of organic molecules in condensed phases. J. Phys. Chem. Ref. Data 15, 1-250.
42. 2+ metal-ion-induced oxidation of methionine in aqueous solution. A pulse radiolysis study. Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 40, 597-604.
43. Eigen, M. (1954) Üeber die Kinetik sehr schnell verlaufender lonenreaktionen in wässeriger Lösung. Z. Phys. Chem. (Leipzig) 203, 176-200.
44. Steinfeld, J. I., J. S. Francisco and W. L. Hase (1989) Chemical Kinetics and Dynamics. Prentice Hall, Englewood Cliffs, NJ.
45. Marcus, R. A. (1960) Theory of oxidation-reduction reactions involving electron transfer. Part 4. A statistical-mechanical basis for treating contributions from solvent, ligands, and inert salt. Discuss. Faraday Soc. 29, 21-31.
46. Marcus, R. A. (1964) Chemical and electrochemical electron-transfer theory. Annu. Rev. Phys. Chem. 15, 155-196.
47. Encinas, M. V., P. J. Wagner and J. C. Scaiano (1980) Hydrogen abstraction by biradicals. Reactions with tri-n-butylstannane and octanethiol. J. Am. Chem. Soc. 102, 1357-1360.
48. 2O. J. Inorg. Biochem. 55, 87-99.
49. Miller, B. L., K. Kuczera and C. Schöneich (1998) One-electron photooxidation of N-methionyl peptides. Mechanism of sulfoxide and azasulfonium diastereomer formation through reaction of sulfide radical cation complexes with oxygen or superoxide. J. Am. Chem. Soc. 120, 3345-3356.
50. Perrin, D. D. (1972) Dissociation Constants of Organic Bases in Aqueous Solution: Supplement 1972. Butterworths, London.
51. Noyes, R. M. (1961) Effects of diffusion rates on chemical kinetics. In Progress in Reaction Kinetics, Vol. 1 (Edited by G. Porter), pp. 129-160. Pergamon, New York.
52. Murov, S. L., I. Carmichael and G. L. Hug (1993) Handbook of Photochemistry, 2nd ed. Dekker, New York.