Electron spin resonance study of radiation-induced radicals in polycrystalline oligopeptides containing methionine

Nukleonika

Volumn 45, Issue 1, 2000, Pages 93-100

  Strzelczak, Grazyna ^b   Bobrowski, Krzysztof ^b   Kozubek, Halina ^a   Michalik, Jacek ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b INSTITUTE OF NUCLEAR CHEMISTRY AND TECHNOLOGY   (Poland)

Author keywords

ESR; Polycrystalline oligopeptides; Radicals

Indexed keywords

EID: 0040197938     PISSN: 00295922     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. Ahern TJ, Manning MC (eds) (1992) Stability of protein pharmaceuticals, parts A and B, Plenum Press, New York
2. Armstrong DA, Yu D, Rauk A (1996) 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. Can J Chem 74:1192-1199
3. Bobrowski K, Holcman J (1989) Formation and stability of intramolecular three-electron S∴N, S∴S, and S∴O bonds in one-electron-oxidized simple methionine peptides. Pulse radiolysis study. J Phys Chem 93:6381-6387
4. 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
5. ̇OH radical induced decarboxylation of methionine-containing peptides. Influence of peptide sequence and net charge. J C S Perkin Trans 2:353-362
6. Bonifačić M, Śtefanić I, Hug GL, Armstrong DA, Asmus K-D (1998) Glycine decarboxylation: the free radical mechanism. J Am Chem Soc 120:9930-9940
7. Burlińska G, Michalik J, Bobrowski K (1994) An electron spin resonance study of gamma-irradiated polycrystalline methionine-containing peptides. Radiat Phys Chem 43:425-432
8. Burlińska G, Wa̧sowicz T, Michalik J, Bobrowski K (1994) Radiation induced radicals in solid peptides. Mol Phys Rep 6:134-139
9. Champagne MH, Mullins MW, Colson A-O, Sevilla MD (1991) Electron spin resonance. Evidence for intra-and intermolecular σσ* bonding in methionine radicals: relative stabilities of S-Cl, S-Br, S-N and S-S three electron bond. J Phys Chem 95:6487-6493
10. Close DM, Anderson R (1973) Ultraviolet photobleaching of free radicals created in γ-irradiated amino acids. Radiat Res 53:349-357
11. D'Arcy JB, Sevilla MD (1979) An electron spin resonance study of electron reactions with peptides: competitive mechanisms. Deamination vs. protonation. Radiat Phys Chem 13:1 19-126
12. Davies KJA (1991) Oxidative damage and repair: chemical, biological and medical aspects, Pergamon Press, New York
13. Drew RC, Gordy W (1963) Electron spin resonance studies of radiation effects on polyamino acids. Radiat Res 18:552-579
14. Floyd RA (1993) Basic free radical biochemistry. In: Byung Pal Yu (eds) Free radicals in aging, CRC Press, Boca Raton, pp 39-55
15. Garrison WM (1987) Reaction mechanism in the radiolysis of peptides, polypeptides, and proteins. Chem Rev 87:381-398
16. Hill DJT, Garrett RW, Ho SY, O'Donnell JH, O'Sullivan PW, Pomery PJ (1981) Radiolysis of model polypeptides in the solid state: radiation sensitivity and side chain structure. Radiat Phys Chem 17:163-171
17. Kawatsura K, Ozawa K, Kominami S, Akasaka K, Hatano H (1974) Optical and ESR studies in N-acetyl DL-methionine single crystals γ-irradiated at low temperature. Radiat Effects 22:267-275
18. Kirino Y, Taniguchi H (1976) An ESR study of the acid dissociation of NH protons. 1. Linear peptide radicals and related radicals. J Am Chem Soc 98:5089-5096
19. Kominami S (1972) A radical cation produced in a γ-irradiated single crystal of DL-methionine as studied by electron spin resonance and optical absorption spectroscopy. J Phys Chem 76:1729-1733
20. Livingston R, Doherty DG, Zeldes H (1975) Electron spin resonance study of liquids during photolysis. XIX. Aliphatic dipeptides. J Am Chem Soc 97:3198-3203
21. Makino K, Riesz P (1982) ESR of spin-trapped radicals in γ-irradiated polycrystalline amino acids. Chromatographic separation of radicals. Int J Radiat Biol 41:615-624
22. Makino K, Riesz P (1982) Electron spin resonance of spin trapped radicals in γ-irradiated polycrystalline dipeptides. Chromatographie separation of radicals. Can J Chem 60:1480-1485
23. Manning MC, Patel K, Borchardt RT (1989) Stability of protein pharmaceuticals. Pharm Res 6:903-917
24. 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
25. Miller BL, Kuczera K, Schöneich Ch (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
26. Minegishi A, Bergene R, Riesz P (1980) ESR of spin-trapped radicals in γ-irradiated polycrystalline amino acids, N-acetyl amino acids and dipeptides. Int J Radiat Biol 38:627-650
27. Rauk A, Yu D, Armstrong DA (1997) 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. J Am Chem Soc 119:208-217
28. Rauk A, Yu D, Armstrong DA (1998) Oxidative damage to and by cysteine in proteins: an ab initia study of the radical structures, C-H, S-H, and C-C bond dissociation energies, and transition structures for H abstraction by thiyl radicals. J Am Chem Soc 120:8848-8855
29. Schöneich Ch, 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
30. Schöneich Ch, Hageman MJ, Borchardt RT (1997) Stability of peptides and proteins. In: Controlled drug delivery. Challenges and strategies. Am Chem Soc, New York, pp 205-228
31. Sevilla M (1970) Radicals formed by the reaction of electrons with amino acids in an alkaline glass. J Phys Chem 74:2096-2102
32. Sevilla MD (1970) Radicals formed by electron attachment to peptides. J Phys Chem 74:3366-3372
33. Sevilla M, D'Arcy JB, Morehouse K (1979) An electron spin resonance study of γ-irradiated frozen aqueous solutions containing dipeptides. Mechanism of radical reaction. J Phys Chem 83:2887-2892
34. Sinclair J, Codella P (1973) Radiation damage produced in single crystals at N-acetylglycine. J Chem Phys 59:1569-1576
35. Stadtman ER (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu Rev Biochem 62:797-821
36. Stenkamp RE, Jensen LH (1974) The crystal structure of D,L-alanyl-L,D-methionine. Acta Cryst B30:1541 -1545
37. Stenkamp RE, Jensen LH (1975) The crystal structure of L-methionyl-L-methionine. Acta Cryst B31:857-861
38. Strzelczak-Burlińska G, Bobrowski K, Pogocki D, Michalik J (1997) ESR study of radiation induced radicals in polycrystalline methionine and its homopeptides. Nukleonika 42:333-342
39. Torchinsky YuM (1979) Sulfur in proteins. Pergamon Press, Oxford