Theoretical study of through-space and through-bond electron transfer within positively charged peptides in the gas phase

International Journal of Mass Spectrometry

Volumn 269, Issue 3, 2008, Pages 149-164

  Sobczyk, Monika ^a   Neff, Diane ^a   Simons, Jack ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Disulfide cleavage; Electron transfer; Electron transfer dissociation

Indexed keywords

EID: 37249055090     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2007.10.003     Document Type: Article

References (49)

1. Zubarev R.A., Kelleher N.L., and McLafferty F.W. J. Am. Chem. Soc. 120 (1998) 3265
2. Zubarev R.A., Kruger N.A., Fridriksson E.K., Lewis M.A., Horn D.M., Carpenter B.K., and McLafferty F.W. J. Am. Chem. Soc. 121 (1999) 2857
3. Zubarev R.A., Horn D.M., Fridriksson E.K., Kelleher N.L., Kruger N.A., Lewis M.A., Carpenter B.K., and McLafferty F.W. Anal. Chem. 72 (2000) 563
4. Zubarev R.A., Haselmann K.F., Budnik B., Kjeldsen F., and Jensen F. Eur. J. Mass Spectrom. 8 (2002) 337
5. Syka J.E.P., Coon J.J., Schroeder M.J., Shabanowitz J., and Hunt D.F. Proc. Natl. Acad. Sci. 101 (2004) 9523
6. Coon J.J., Syka J.E.P., Schwartz J.C., Shabanowitz J., and Hunt D.F. Int. J. Mass Spectrom. 236 (2004) 33
7. Pitteri S.J., Chrisman P.A., and McLuckey S.A. Anal. Chem. 77 (2005) 5662
8. Gunawardena H.P., He M., Chrisman P.A., Pitteri S.J., Hogan J.M., Hodges B.D.M., and McLuckey S.A. J. Am. Chem. Soc. 127 (2005) 12627
9. Syrstad E.A., and Turecek F. J. Phys. Chem. A105 (2001) 11144
10. Turecek F., Polasek M., Frank A., and Sadilek M. J. Am. Chem. Soc. 122 (2000) 2361
11. Syrstad E.A., Stephens D.D., and Turecek F. J. Phys. Chem. A107 (2003) 115
12. Turecek F. J. Am. Chem. Soc. 125 (2003) 5954
13. Syrstad E.A., and Turecek F. Am. Soc. Mass Spectrom. 16 (2005) 208
14. Uggerud E. Int. J. Mass Spectrom. 234 (2004) 45
15. Anusiewicz I., Berdys-Kochanska J., and Simons J. J. Phys. Chem. A109 (2005) 5801
16. Anusiewicz I., Berdys-Kochanska J., Skurski P., and Simons J. J. Phys. Chem. A110 (2006) 1261
17. Sawicka A., Skurski P., Hudgins R.R., and Simons J. J. Phys. Chem. B107 (2003) 13505
18. Sobczyk M., Skurski P., and Simons J. Adv. Quantum Chem. 48 (2005) 239
19. Sawicka A., Berdys-Kochaska J., Skurski P., and Simons J. Int. J. Quantum Chem. 102 (2005) 838
20. Anusiewicz I., Berdys J., Sobczyk M., Sawicka A., Skurski P., and Simons J. J. Phys. Chem. A109 (2005) 250
21. Bakken V., Helgaker T., and Uggerud E. Eur. J. Mass Spectrom. 10 (2004) 625
22. Skurski P., Sobczyk M., Jakowski J., and Simons J. Int. J. Mass Spectrom. 265 (2007) 197
23. Gunawardena H.P., Gorenstein L., Erickson D.E., Xia Y., and McLuckey S.A. Int. J. Mass Spectrom. 265 (2007) 130
24. Dezarnaud-Dandine C., Bournel F., Troncy M., Jones D., and Modelli A. J. Phys. B: At. Mol. Opt. Phys. 31 (1998) L497
25. Seydou M., Modelli A., Lucas B., Konate K., Desfrancois C., and Schermann J.P. Eur. Phys. J. D 35 (2005) 199
26. Hudgins R., Håkansson K., Quinn J.P., Hendrickson C.L., and Marshall A.G. Proceedings of the 50th ASMS Conference on Mass Spectrometry and Allied Topics. Orlando, Florida, June 2-6 (2002) A020420 Fig. 1 first appears in publication in Ref. [3i]
27. The workers of Ref. [3i] cite the following reference in support of this claim:. Hudgins R.R., and Jarrold M.F. J. Am. Chem. Soc. 121 (1999) 3494 In this paper, a singly-charged analog of the species shown in Fig. 1 was used and found to display extended rather than compact structure, suggesting that the doubly-charged species would also be extended because it would also have internal Coulomb repulsion between the two positive Lys sites
28. A more recent effort aimed at using mobility measurements to probe extended and more compact structures of alanine-containing peptides is given in. Counterman A.E., and Clemmer D.E. J. Phys. Chem. B 107 (2003) 2111
29. Sobczyk M., and Simons J. J. Phys. Chem. B 110 (2006) 7519
30. Sobczyk M., and Simons J. Int. J. Mass Spectrom. 253 (2006) 274
31. 3 Rydberg radicals, the ground-Rydberg state is labeled with n = 3 principal quantum number because the nitrogen 1s and four bonding electron pairs occupy 1s, 2s, and 2p orbitals in the united-atom limit, so the Rydberg electron resides in an n = 3 orbital. So, the excited Rydberg orbital shown has n = 4.
32. The geometries shown in Fig. 5 represent those of the minimum-energy structures found using a PM3 force field.
33. α cleavage.
34. See Refs. [8a] and [8b] as well as Ref. [3h].
35. Gutowski M., and Simons J. J. Chem. Phys. 93 (1990) 3874
36. Skurski P., Gutowski M., and Simons J. Int. J. Quantum Chem. 80 (2000) 1024
37. Kendall R.A., Dunning Jr. T.H., and Harrison R.J. J. Chem. Phys. 96 (1992) 6796
38. See Ref. [3l]. This device was first used in. Nestmann B., and Peyerimhoff S.D. J. Phys. B 18 (1985) 615
39. See Ref. [3l]. This device was first used in. Nestmann B., and Peyerimhoff S.D. J. Phys. B 18 (1985) 4309
40. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
41. Schaftenaar G., and Noordik J.H. J. Comput. Aided Mol. Des. 14 (2000) 123
42. As remarked earlier, for the species studied in the experiments, there are more than two positive charges present. Thus, it is possible that another positive charge may be closer to the S-S bond than to the positive site holding the attached electron and thus may energy-stabilize the S-S σ* curve more than the Rydberg curve. This would then cause the crossing of the σ* and ground-Rydberg curves to occur within the thermally accessible region.
43. See Ref. [3e] as well as. Turecek F., and Reid P.J. Int. J. Mass Spectrom. 222 (2003) 49
44. Turecek F., and Syrstad E.A. J. Am. Chem. Soc. 125 (2003) 3353
45. Nguyen V.Q., Sadilek M., Ferrier J., Frank A.J., and Tureek F. J. Phys. Chem. A 101 (1997) 3789
46. Because Ala is near the S-S bond at and near minimum-energy structures, it is thus likely to be able to effect TS electron transfer during the ca. 10-6 s window of opportunity available to it.
47. To test the degree of steric crowding, it would be useful to repeat the experiments carried out in the McLuckey lab using ECD rather than ETD. In ECD, the free electrons would not be as hindered in reaching the S-S bond site as is the azobenzene anion used in ETD.
48. 3.
49. If, in fact, initial electron transfer to the Ala (or TMAB-substituted Ala) suffers from steric hindrance, the yield of S-S cleavage in this species could be even further lowered.