Transition metals as electron traps. I. Structures, energetics, electron capture, and electron-transfer-induced dissociations of ternary copper-peptide complexes in the gas phase

Journal of Mass Spectrometry

Volumn 44, Issue 5, 2009, Pages 707-724

  Tureček, František ^a   Jones, Jace W ^a   Holm, Anne I S ^b   Panja, Subhasis ^b   Nielsen, Steen Brøndsted ^b   Hvelplund, Preben ^b  

^a UNIVERSITY OF WASHINGTON   (United States)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

Ab initio calculations; Copper peptide complexes; Electron transfer; Electronic states; Ion structures

Indexed keywords

AB INITIO CALCULATIONS; ATOMIC CHARGE; BASIS SETS; BIPYRIDINE; CANONICAL FORM; CHARGED COMPLEXES; CU COMPLEXES; DISSOCIATION PRODUCTS; ELECTRON CAPTURE; ELECTRON CAPTURE DISSOCIATION; ELECTRON STRUCTURES; ELECTRON TRANSFER; ELECTRON-INDUCED DISSOCIATION; GASPHASE; INDUCED DISSOCIATION; ION DISSOCIATIONS; ION STRUCTURES; OPTIMIZED STRUCTURES; PENNING TRAP; PENTACOORDINATED; PEPTIDE BACKBONES; PEPTIDE COMPLEX; PEPTIDE LIGAND; PRECURSOR IONS; SHORT TIME SCALE; SINGLET STATE; SPIN STATE; STRUCTURE CHANGE; TIME-SCALE; TRIPLET ELECTRONIC STATE; TRIPLET STATE; ZWITTERIONIC FORMS;

COPPER; COPPER COMPOUNDS; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTROCHEMICAL SENSORS; ELECTROCHROMIC DEVICES; ELECTROMAGNETIC INDUCTION; ELECTRON TRANSITIONS; ELECTRONIC STATES; LIGANDS; METAL IONS; MOLECULAR STRUCTURE; REDUCTION; SPIN DYNAMICS;

AMINES;

2,2' BIPYRIDINE; COPPER; GLYCINE; LEUCINE;

AMINO ACID SEQUENCE; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; ELECTRON CAPTURE DETECTION; ELECTRON TRANSPORT; ENERGY TRANSFER; EXPERIMENTAL STUDY; FRAGMENTATION REACTION; GAS; INTERMETHOD COMPARISON; ISOMERIZATION; LIGAND BINDING; PRIORITY JOURNAL; PROTEIN STABILITY; PROTEIN STRUCTURE; THERMODYNAMICS;

COPPER; ELECTRONS; GASES; MASS SPECTROMETRY; MODELS, CHEMICAL; OLIGOPEPTIDES;

EID: 66249098552     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1546     Document Type: Article

References (56)

1. C.L.Gatlin, F.Tureček. Electrospray ionization of inorganic and organometallic complexes. In Electrospray Ionization Mass Spectrometry. Fundamentals, Instrumentation & Applications, R. B. Cole (ed). Wiley: New York, 1997, 527.
2. H. Sigel, R. B. Martin. Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chemical Reviews 1982, 82, 385.
3. B. E. Fischer, H. Sigel. Ternary complexes in solution. 35. Intramolecular hydrophobic ligand-ligand interactions in mixed ligand complexes containing an aliphatic amino acid. Journal of the American Chemical Society 1980, 102, 2998.
4. O.Yamauchi, A. Odani. Structure-stability relationship in ternary copper(II) complexes involving aromatic amines and tyrosine or related amino acids. Intramolecular aromatic ring stacking and its regulation through tyrosine phosphorylation. Journal of the American Chemical Society 1985, 107, 5938.
5. O. Yamauchi, K. Tsujide, A. Odani. Copper(II) complexes of tyrosine- containing dipeptides. Effects of side-chain groups on spectral and solution chemical properties and their structural implication. Journal of the American Chemical Society 1985, 107, 659.
6. C. L. Gatlin, F. Tureček, T. Vaisar. Copper(II) amino acid complexes in the gas phase. Journal of the American Chemical Society 1995, 117, 3637.
7. C. L. Gatlin, F. Tureček. Ternary complexes of amino acids with late transition metal cations and diimine ligands in the gas phase. Journal of Mass Spectrometry 1995, 30, 1636.
8. C.L.Gatlin, R.D.Rao, F.Tureček, T.Vaisar. Carboxylate and amine terminus directed fragmentations in gaseous dipeptide complexes with copper(II) and diimine ligands formed by electrospray. Analytical Chemistry 1996, 68, 263.
9. T.Vaisar, C. L. Gatlin, R.D.Rao, J. L.Seymour, F. Tureček. Sequence information, distinction and quantitation of C-terminal leucine and isoleucine in ternary complexes of tripeptides with Cu(II) and 2, 2′-bipyridine. Journal of Mass Spectrometry 2001, 36, 306.
10. I.K.Chu, C. F. Rodriquez, T.C.Lau, A. C. Hopkinson, K.W.M.Siu. Molecular radical cations of oligopeptides. Journal of Physical Chemistry B 2000, 704, 3393.
11. E. Bagheri-Majdi, Y. Ke, G.Orlova, I.K.Chu, A. C. Hopkinson, K. W. M. Siu.Copper-mediated peptideradical ions in thegas phase. Journal of Physical Chemistry B 2004, 108, 11170.
12. C. K. Barlow, S.Wee, W. D. McFadyen, R.A.J.O'Hair. Designing copper(II) ternarycomplexes togenerateradical cations ofpeptides in the gas phase: role of the auxiliary ligand. Dalton Transactions 2004, 3199.
13. T.Vaisar, C.L.Gatlin, F.Tureček. Oxidation of peptide-copper complexes by alkali metal cations in the gas phase. Journal of theAmerican ChemicalSociety1996, 118, 5314.
14. T.Vaisar, C.L.Gatlin, F.Tureček. Metal-ligand redox reactions in gas-phase quaternary peptide-metal complexes by electrospray ionization mass spectrometry. International Journal of Mass SpectrometryandIon Processes 1997, 162, 77.
15. T. Vaisar, J. W. Heinecke, J. L. Seymour, F. Tureček. Copper-mediated intra-ligand oxygen transfer in gas-phase complexes with 3- nitrotyrosine. Journal of Mass Spectrometry 2005, 40, 608.
16. F. Tureček. Copper-biomolecule complexes in the gas phase. The ternary way. Mass Spectrometry Reviews 2007, 26, 563.
17. A.T. lavarone, K. Paech, E. R. Williams. Effects of charge state and cationizing agent on the electron capture dissociation of a peptide. Analytical Chemistry 2004, 76, 2231.
18. Y.M.E.Fung, H.Liu, T.W.D.Chan. Electroncapturedissociationof peptides metalated with alkaline-earth metal ions. Journal of the American Society for Mass Spectrometry 2006, 17, 757.
19. R.A.Zubarev, N. L. Kelleher, F. W. McLafferty. Electron capture dissociation of multiply charged protein cations. A nonergodic process. JournaloftheAmerican ChemicalSociety1998, 120, 3265.
20. H. Liu, K. Hakansson. Divalent metal ion-peptide interactions probed by electron capture dissociation of trications. Journal of theAmerican SocietyforMassSpectrometry2006, 17, 1731.
21. H. Liu, K. Hakansson. Electron capture dissociation of tyrosine O- sulfated peptides complexed with divalent metal cations. Analytical Chemistry 2006, 78, 7570.
22. A.J.Kleinnijenhuis, R.Mihalca, R.M.A.Heeren, A.J.R.Heck. Atypical behavior in the electron capture induced dissociation of biologically relevant transition metal ion complexes of the peptide hormoneoxytocin. InternationalJournalofMassSpectrometry2006, 253, 217.
23. M. O. Larsson, P. Hvelplund, M. C. Larsen, H. Shen, H. Cederquist, H.T.Schmidt. Electron capture and energy loss in ∼100keV collisions ofatomic and molecular ions on C60. InternationalJournal ofMassSpectrometry1998, 177, 51.
24. C. A. Schalley, G. Hornung, D. Schroder, H.Schwarz. Mass spectrometry as a tool to probe the gas phase reactivity of neutral molecules. International Journal of Mass Spectrometryand Ion Processes 1998, 172, 181.
25. + potential energy surface. Chemistry- A European Journal 1997, 3, 626.
26. D. Schroder. Neutralization, charge reversal. The Encyclopedia of Mass Spectrometry, vol. 1, Chapter 8, P. B. Armentrout (ed). Elsevier: Amsterdam, 2003, pp 521.
27. P. Hvelplund, B. Liu, S. B. Nielsen, S. Panja, J. C. Poully, K. Støchkel. Electron capture induced dissociation of peptide ions: identification of neutral fragments from secondary collisions with cesium vapor. International Journal of Mass Spectrometry 2007, 263, 66.
28. S. Hayakawa, M. Hashimoto, H. Matsubara, F. Tureček. Dissecting the proline effect: dissociations of proline radicals formed by electron transfer to protonated Pro-Gly and Gly-Pro dipeptides in the gas phase. Journal of the American Chemical Society 2007, 129, 7936.
29. S.Hayakawa, H.Matsubara, S.Panja, P.Hvelplund, S.B.Nielsen, X.Chen, F. Tureček. Experimental evidence for an inverse hydrogen migration in arginine radicals. Journal of the American Chemical Society 2008, 130, 7645.
30. P.Caravatti, M. Allemann. The infinity cell-A new trapped-ion cell with radiofrequency covered trapping electrodes for Fourier- transform ion-cyclotron resonance mass spectrometry. Organic Mass Spectrometry 1991, 26, 514.
31. 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 03, Revision B.05, Gaussian: Pittsburgh, 2003.
32. P.J. Hay, W. R. Wadt.Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms scandium to mercury. Journal of Chemical Physics 1985, 82, 270.
33. P.J. Hay, W. R. Wadt.Ab initio effective core potentials for molecular calculations. Potentials for potassium to gold including the outermost core orbitals. Journal of Chemical Physics 1985, 82, 299.
34. D. R. Lide (ed). CRCHandbookof Chemistry and Physics, 88th ed. CRC Press: Boca Raton, FL, 2007-2008, 10 10.
35. C. Møller, M. S. Plesset. A Note on an approximation treatment for many-electron systems. Physical Review 1934, 46, 618.
36. R. E. Stratmann, G. E. Scuseria, M.J. Frisch. An efficient implementation of time-dependent density functional theory for the calculation of excitation energies of large molecules. Journalof Chemical Physics 1998, 109, 8218.
37. A. E. Reed, R. B. Weinstock, F. Weinhold.Natural population analysis. Journal of Chemical Physics 1985, 83, 735.
38. P. Hvelplund, B. Liu, S. B. Nielsen, S. Tomita. Electron capture induced dissociation of peptide dications. International Journal of Mass Spectrometry 2003, 225, 83.
39. A. I. S. Holm, P. Hvelplund, U.Kadhane, M. K. Larsen, B.Liu, S.B.Nielsen, S. Panja, J. M. Pedersen, T. Skrydstrup, K. Stachkel, E. R. Williams, E. S. Worm. On the mechanism of electron-capture- induced dissociation of peptide dications from 15N-labeling and crown-ether complexation. Journal of Physical Chemistry A 2007, 111, 9641.
40. S. Hayakawa, M. Hashimoto, H. Nagao, K. Awazu, M. Toyoda, T. Ichihara, Y. Shigeri. Studyofthe dissociation of a charge-reduced phosphopeptide formed by electron transfer from an alkali metal target. Rapid Communications in Mass Spectrometry 2008, 22, 567.
41. F.Tureček. The modern mass spectrometer. A laboratory for unstable neutral species. Organic Mass Spectrometry 1992, 27, 1087.
42. F.Tureček. Transient intermediates of chemical reactions by neutralization-reionization mass spectrometry. Topics in Current Chemistry 2003, 225, 77.
43. S.A.Shaffer, M. Sadílek, F.Tureček. Hypervalent ammonium radicals. Effects of Alkyl groups and aromatic substituents. Journal of Organic Chemistry 1996, 61, 5234.
44. V. Q. Nguyen, M. Sadílek, A.J. Frank, J.G. Ferrier, F. Tureček. Metastable states of dimethylammonium radical. Journal of Physical Chemistry A 1997, 101, 3789.
45. 2OH. International Journal of Mass Spectrometry 2003, 222, 49.
46. M. Sobczyk, I. Anusiewicz, J. Berdys-Kochanska, A. Sawicka, P. Skurski, J. Simons. Coulomb-assisted dissociative electron attachment: application to a model peptide. Journal of Physical Chemistry A 2005, 109, 250.
47. M. Sobczyk, J. Simons. The roleof excited rydberg states in electron transfer dissociation. Journal of Physical Chemistry B 2006, 110, 7519.
48. M. Sobczyk, D. Neff, J. Simons. Theoretical study of through-space and through-bond electron transfer within positively charged peptides in the gas phase. International Journal of Mass Spectrometry 2008, 269, 149.
49. E. A. Syrstad, F. Tureček. Toward a general mechanism of electron- capture dissociation. Journal of the American Society for Mass Spectrometry 2005, 16, 208.
50. F.Tureček, X. Chen, C. Hao. Where does the electron go? electron distribution and reactivity of peptide cation radicals formed by electron transfer in the gas phase. Journal of the American Chemical Society 2008, 130, 8818.
51. S. Hayakawa. Charge inversion mass spectrometry: dissociation of resonantly neutralized molecules. Journal of Mass Spectrometry 2004, 39, 111.
52. +). Journal of Physical Chemistry 2004, 108, 14407.
53. F. Basolo, J. C. Hayes, H. M. Neumann. Mechanism of racemization of complexions. I. Kinetics of the dissociation and racemization of tris-(1, 10-phenanthroline)nickel(II) and tris - (2, 2′ - bipyridyl)nickel(II) complexes. Journal of the American Chemical Society 1953, 75, 5102.
54. F.Tureček, E. A. Syrstad. Mechanism and energetics of intramolecular hydrogen transfer atom transfer in amide and peptide radicals and cation-radicals. Journal of the American Chemical Society 2003, 125, 3353.
55. α Bond dissociation energiesand kinetics in amide and peptide radicals. Is the dissociation a non-ergodic process? Journal of the American Chemical Society 2003, 125, 5954.
56. N. Leymarie, C.E.Costello, P.B. O'Connor. Electron capture dissociation initiates a free radical reaction cascade. Journal of theAmerican ChemicalSociety2003, 125, 8949.