pH effects on the photooxidation of methionine derivatives by the 4-carboxybenzophenone triplet state

Nukleonika

Volumn 45, Issue 1, 2000, Pages 63-71

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

^a UNIVERSITY OF NOTRE DAME   (United States)

^b INSTITUTE OF NUCLEAR CHEMISTRY AND TECHNOLOGY   (Poland)

^c ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Electron transfer; Flash photolysis; pH efects; Photochemistry; Quantum yields; Radical ions

Indexed keywords

EID: 0013080338     PISSN: 00295922     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Guttenplan JB, Cohen SG (1973) Quenching and reduction of photoexcited benzophenone by thioethers and mercaptans. J Org Chem 38:2001-2007
2. Cohen SG, Ojanpera S (1975) Photooxidation of methionine and related compounds. J Am Chem Soc 97:5633-5634
3. Bobrowski K, Marciniak B, Hug GL (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
4. Bobrowski K, Marciniak B, Hug GL (1994) A reinvestigation of the mechanism of photoreduction of benzophenones by alkyl sulfides. J Photochem Photobiol A 81:159-168
5. Bobrowski K, Hug GL, Marciniak B, Kozubek H (1994) 4-Carboxybenzophenone-sensitized photooxidation of sulfur-containing amino acids in alkaline aqueous solutions. Secondary photoreactions kinetics. J Phys Chem 98:537-544
6. Marciniak B, Bobrowski K, Hug GL, Rozwadowski J (1994) Photoinduced electron transfer between sulfur-containing carboxylic acids and the 4-carboxybenzophenone triplet state in aqueous solution. J Phys Chem 98:4854-4860
7. Marciniak B, Hug GL, Bobrowski K, Kozubek H (1995) Mechanism of 4-carboxybenzophenone-sensitized photooxidation of methionine-containing dipeptides and tripeptides in aqueous solution. J Phys Chem 99:13560-13568
8. Bobrowski K, Hug GL, Marciniak B, Miller BL, Schöneich C (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
9. Bobrowski K, Schöneich C (1993) Hydroxyl radical adduct at sulfur in substituted organic sulfides stabilized by internal hydrogen bond. J Chem Soc Chem Commun 795-797
10. Schöneich C, Zhao F, Madden KP, Bobrowski K (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
11. Davies KJA (ed) (1992) Oxidative damage and repair. Chemical, biological, and medicinal aspects. Pergamon Press, New York
12. Asmus K-D, Bonifacic M (1994) Free radical chemistry. In: Sen CK, Packer L, Hanninen O (eds) Exercise and oxygen toxicity. Elsevier, Amsterdam, pp 1-47
13. Fridovich I (1995) Superoxide radical and superoxide dismutases. Annu Rev Biochem 64:97-112
14. Cleland JL, Powell MF, Shire SJ (1993) The development of stable protein formulations. A close look at protein aggregation, deamidation, and oxidation. Crit Rev Ther Drug Carrier Syst 10:307-377
15. Hug GL, Bobrowski K, Kozubek H, Marciniak B (1998) Photooxidation of methionine derivatives by the 4-carboxybenzophenone triplet state in aqueous solution. Intra-complex proton transfer involving the amino group. Photochem Photobiol 68:785-796
16. Asmus K-D (1979) Stabilization of oxidized sulfur centers in organic sulfides. Radical cations and odd-electron sulfur-sulfur bonds. Acc Chem Res 12:436-442
17. 2 with X = C1, Br, I, and SCN. J Phys Chem 89:2330-2335
18. Janata E (1981) "SR59: A pulse generator for pulsing xenon lamps" SR59 (Radiation Laboratory)
19. + radical cation. J Phys Chem 100:14914-14921
20. Carmichael I, Hug GL (1986) Triplet-triplet absorption spectra of organic molecules in condensed phases. J Phys Chem Ref Data 15:1-250