Lysine Peroxycarbamates: Free Radical-Promoted Peptide Cleavage

Journal of the American Chemical Society

Volumn 126, Issue 3, 2004, Pages 720-721

  Masterson, Douglas S ^a   Yin, Huiyong ^a   Chacon, Almary ^a   Hachey, David L ^a   Norris, Jeremy L ^a   Porter, Ned A ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; FREE RADICAL; LITHIUM; LYSINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTEIN ANALYSIS; PROTEIN DEGRADATION; SEQUENCE ANALYSIS;

AMINO ACID SEQUENCE; CARBAMATES; FREE RADICALS; LYSINE; MOLECULAR SEQUENCE DATA; PEPTIDE MAPPING; PEPTIDES; PEROXIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 1642453599     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038615u     Document Type: Article

References (19)

1. Yates, J. R. J. Mass. Spectrom. 1998, 33, 1-19.
2. Aebersold, R.; Goodlett, D. R. Chem. Rev. 2001, 101, 269-295.
3. (a) Glocker, M. O.; Borchers, C.; Fieldler, A.; Suckau, D.; Przybylski, M. Bioconjugate Chem. 1994, 5, 583-590
4. (b) Bonetto, V.; Bergman, A.; Joernvall, H.; Sillard, R. Anal. Chem. 1997, 69, 1315-1319.
5. (c) Aebersold, R.; Goodlett, D. R. Chem. Rev. 2001, 101, 269-295.
6. McLuckey, S. A.; Reid, G. E. J. Mass. Spectrom. 2002, 37, 663-675.
7. Kelleher, N. L.; Lin, H. Y.; Valaskovic, G. A.; Aaserud, D. J.; Fridriksson, E. K.; McLafferty, F. W. J. Am. Chem. Soc. 1999, 121, 806.
8. Bourgeois, M. J.; Campagnole, M.; Filliatre, C.; Maillard, B.; Manigand, C.; Villenave, J. J. Tetrahedron 1982, 38, 3569-3577.
9. Usual precautions regarding peroxides were followed for compounds 1 and 2.
10. The half-life of 1 in pH 8.2 phosphate buffer (50% MeOH) is approximately 112 s. Details of the kinetics will be published in due course.
11. m+.
12. (a) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095-7129.
13. For a discussion of the chemistry of protein aminyl radicals, see: (b) Hawkins, C, L.; Davies, M. J. Biochim. Biophys. Acta. 2001, 1504, 196-219.
14. See also: (a) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J. O. Angew. Chem., Int. Ed. 2002, 41, 2738-2742.
15. (b) Julian, R. R.; May, J. A.; Stoltz, B. M.; Beauchamp, J. L. Angew. Chem., Int. Ed. 2003, 42, 1012-1015.
16. (c) Yin, H.; Hachey, D. L.; Porter, N. A. J. Am. Soc. Mass Spectrom. 2001, 12, 449-455.
17. Free radicals have been suggested in the electron capture chemistry of peptides and proteins. See, for example: (a) Leymarie, N.; Costello, C. E.; O'Connor, P. B. J. Am. Chem. Soc. 2003; 125, 8949-8958.
18. (b) Syrstad, E. A.; Stephens, D. D.; Turecek, F. J. Phys. Chem. A 2003, 107, 115.
19. (c) Turecek, F.; Syrstad, E. A. J. Am. Chem. Soc. 2003, 125, 3353.