Phenyl radical-induced damage to dipeptides

Journal of Organic Chemistry

Volumn 74, Issue 20, 2009, Pages 7724-7732

  Li, Sen ^a,b   Fu, Mingkun ^a   Habicht, Steven C ^a   Pates, George O ^a   Nash, John J ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

^b EASTMAN CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID SEQUENCE; AROMATIC SIDE CHAINS; CHEMICAL EQUATIONS; DI-PEPTIDES; ELECTROPHILICITY; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY; GASPHASE; INDUCED DAMAGE; LASER-INDUCED ACOUSTIC DESORPTIONS; N-TERMINALS; PHENYL RADICALS; POSITIVELY CHARGED; PRODUCT BRANCHING RATIOS; SIDE CHAINS;

AMINES; AMINO ACIDS; CHEMICAL REACTIONS; DESORPTION; MASS SPECTROMETRY; ORGANIC ACIDS;

ATOMS;

AROMATIC COMPOUND; BENZENE DERIVATIVE; DIPEPTIDE; HYDROGEN;

AMINO ACID SEQUENCE; ARTICLE; ATOM; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; CHEMICAL STRUCTURE; DESORPTION; FOURIER TRANSFORMATION; GAS; ION CYCLOTRON RESONANCE MASS SPECTROMETRY;

DIPEPTIDES; FREE RADICALS; HYDROXYL RADICAL; MOLECULAR STRUCTURE; PHENOL;

EID: 70349883630     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901470f     Document Type: Article

References (34)

1. (a) Garrison, M. W. Radiat. Res. Rev. 1972, 3, 305.
2. (b) Easton, J. C. Chem. Rev. 1997, 97, 53.
3. (c) Davies, J. M.; Fu, S.; Wang, H.; Dean, T. R. Free Radical Biol. Med. 1999, 27, 513.
4. (d) Garrison, W. M. Chem. Rev. 1987, 87, 381.
5. (e) Davies, M. J. Dea, R. T. Radical-Mediated Protein Oxidation: From Chemistry to Medicine; Oxford University Press: Oxford, 1997.
6. (f) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746.
7. (g) Griffiths, J.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1992, 1, 24.
8. (h) Davies, J. M.; Fu, S.; Wang, H.; Dean, R. T. Free Radical Biol. Med. 1999, 27, 1151.
9. (i) Dean, T. R.; Fu, S.; Stocker, R.; Davis, J. M. Biochem. J. 1997, 324, 1.
10. (j) Hawkins, C. L.; Davies, M. J. Biochim. Biophys. Acta 2001, 1504, 196.
11. (k) Hawkins, C. L.; Davies, M. J. Chem. Soc., Perkins Trans. 2 1998, 1937.
12. (a) Davies, J. K. J. Biol. Chem. 1987, 262, 9895.
13. (b) Goshe, B. M.; Chen, H. Y.; Anderson, E. V. Biochemistry 2000, 39, 1761.
14. (c) Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513.
15. (d) Deterding, L. J.; Barr, D. P.; Mason, R. P.; Tomer, K. B. J. Biol. Chem. 1998, 273, 12863.
16. (e) Bonifačić, M.; Štefanić, I.; Hug, G. L.; Armstrong, D. A.; Asmus, K.-D. J. Am. Chem. Soc. 1998, 120, 9930.
17. (f) Nukuna, B. N.; Goshe, M. B.; Anderson, V. E. J. Am. Chem. Soc. 2001, 123, 1208.
18. (g) Štefanić, I.; Bonifačić, M.; Asmus, K.-D.; Armstrong, D. A. J. Phys. Chem. A 2001, 105, 8681.
19. (a) Braslau, R.; Anderson, M. O. Tetrahedron Lett. 1998, 39, 4227.
20. (b) Sun, Q.; Nelson, H.; Ly, T.; Stoltz, B. M.; Julian, R. R. J. Proteome Res. 2009, 8, 958.
21. (a) Stirk, K. G.; Kenttämaa, H. I. J. Am. Chem. Soc. 1991, 113, 5880.
22. (b) Chyall, L. J.; Kenttämaa, H. I. J. Am. Chem. Soc. 1994, 116, 3135.
23. (c) Li, R.; Smith, R. L.; Kenttämaa, H. I. J. Am. Chem. Soc. 1996, 118, 5056.
24. (d) Ramirez-Arizmendi, L. E.; Heidbrink, J. L.; Guler, L. P.; Kenttämaa, H. I. J. Am. Chem. Soc. 2003, 125, 2272.
25. (e) Radical Reactions as Modeled by Distonic Ions. In Encyclopedia of Mass Spectrometry: Fundamentals and Applications to Organic and Organometallic Compounds; Kenttämaa, H. I., Nibbering, N. N. M., Gross, M. L., Caprioli, R., Eds. Elsevier: New York, 2005.
26. (a) Huang, Y.; Guler, L.; Heidbrink, J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2005, 127, 3973.
27. (b) Huang, Y.; Kenttämaa, H. I. J. Am. Chem. Soc. 2005, 127, 7952.
28. Note that, for these calculations, the vertical electron affinity of the radical site, not the vertical electron affinity of the molecule, is computed.
29. (a) Petzold, C. J.; Ramirez-Arizmendi, L. E.; Heidbrink, J. L.; Kenttämaa, H. I. J. Am. Soc. Mass Spectrom. 2002, 13, 192.
30. (b) Pérez, J.; Ramírez-Arizmendi, L. E.; Petzold, C. J.; Guler, L. P.; Nelson, E. D.; Kenttämaa, H. I. Int. J. Mass Spectrom. 2000, 198, 173.
31. (c) Shea, R. C.; Petzold, C. J.; Campbell, J. L.; Li, S.; Aaserud, D. J.; Kenttämaa, H. I. Anal. Chem. 2006, 78, 6133.
32. Thoen, K. K.; Kenttämaa, H. I. J. Am. Chem. Soc. 1999, 121, 800.
33. Jing, L.; Nash, J. J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2008, 130, 17697.
34. Yu, D.; Rauk, A.; Yu, D.; Armstrong, D. A. J. Am. Chem. Soc. 1995, 117, 1789.