Inverse Hydrogen Migration in Arginine-Containing Peptide Ions upon Electron Transfer

Journal of the American Society for Mass Spectrometry

Volumn 19, Issue 12, 2008, Pages 1726-1742

  Panja, Subhasis ^a   Nielsen, Steen Brøndsted ^a   Hvelplund, Preben ^a   Tureček, František ^b  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; AMINO ACIDS; AMMONIUM COMPOUNDS; ARGON; ATOMIC PHYSICS; ATOMS; CESIUM; CESIUM COMPOUNDS; DISSOCIATION; ELECTROLYSIS; ELECTRON TRANSITIONS; ELECTRONIC PROPERTIES; ELECTRONIC STATES; ELECTRONIC STRUCTURE; ELECTRONS; HYDROGEN; IONS; ISOMERS; NEGATIVE IONS; POTENTIAL ENERGY; POTENTIAL ENERGY SURFACES; QUANTUM CHEMISTRY; RATE CONSTANTS; SURFACE STRUCTURE;

BOND CLEAVAGES; CARBOXYL GROUPS; ELECTRON ATTACHMENTS; ELECTRON DENSITIES; ELECTRON TRANSFERS; ELECTRONIC STRUCTURE THEORIES; GUANIDINIUM; HYDROGEN ATOMS; HYDROGEN MIGRATIONS; INTERNAL ENERGIES; PEPTIDE IONS; PROTONATED; PROTONATED PEPTIDES; SINGLE BONDS; STATE ENERGIES; TIME SCALES;

FREE RADICAL REACTIONS;

AMIDE; AMMONIA; ARGININE; GUANIDINE; PEPTIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; DISSOCIATION CONSTANT; ELECTRON TRANSPORT; ENERGY TRANSFER; HYDROGEN BOND; ISOMERIZATION; MASS SPECTROMETRY; PROTON TRANSPORT;

ARGININE; DIPEPTIDES; ELECTRON TRANSPORT; HYDROGEN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STATIC ELECTRICITY;

EID: 56949088831     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.08.001     Document Type: Article

References (57)

1. Wysocki V.H., Tsapralis G., Smith L.L., and Breci L.A. Mobile and Localized Protons: A Framework for Understanding Peptide Dissociation. J. Mass Spectrom 35 (2000) 1399-1406
2. Cooper H.J., Hudgins R.R., Hakansson K., and Marshall A.G. The Role of Electron Capture Dissociation in Biomolecular Analysis. J. Am. Soc. Mass Spectrom 13 (2002) 241-249
3. Cooper H.J. Investigation of the Presence of b Ions in Electron Capture Dissociation Mass Spectra. J. Am. Soc. Mass Spectrom 16 (2005) 1932-1940
4. Fung Y.M.E., Duan L., and Chan T.W.D. A Comparative Study of the Collision-Induced Dissociation and the Electron Capture Dissociation of Model Peptides Using Electrospray Ionization Fourier-Transform Mass Spectrometry. Eur. J. Mass Spectrom 10 (2004) 449-457
5. Xia Y., Gunawardena H.P., Erickson D.E., and McLuckey S.A. Effects of Cation Charge-Site Identity and Position on Electron-Transfer Dissociation of Polypeptide Cations. J. Am. Chem. Soc 129 (2007) 12232-12243
6. Fung Y.M.E., and Chan T.-W.D. Experimental and Theoretical Investigations of the Loss of Amino Acid Side Chains in Electron Capture Dissociation of Model Peptides. J. Am. Soc. Mass Spectrom 16 (2005) 1523-1535
7. Zubarev R.A., Kelleher N.L., and McLafferty F.W. Electron Capture Dissociation of Multiply Charged Protein Cations. A Nonergodic Process. J. Am. Chem. Soc 120 (1998) 3265-3266
8. Syka J.E.P., Coon J.J., Schroeder M.J., Shabanowitz J., and Hunt D.F. Peptide and Protein Sequence Analysis by Electron Transfer Dissociation Mass Spectrometry. Proc. Natl. Acad. Sci. U. S. A 101 (2004) 9528-9533
9. Hayakawa S., Matsubara H., Panja S., Hvelplund P., Nielsen S.B., Chen X., and Tureček F. Experimental Evidence for an Inverse Hydrogen Migration in Arginine Radicals. J. Am. Chem. Soc 130 (2008) 7645-7654
10. Hao C., Seymour J.L., and Tureček F. Electron Super-Rich Radicals in the Gas Phase. A Neutralization-Reionization Mass Spectrometric and Ab Initio/RRKM Study of Diaminohydroxymethyl and Triaminomethyl Radicals. J. Phys. Chem. A 111 (2007) 8829-8843
11. Yu D., Rauk A., and Armstrong D.A. Radicals and Ions of Glycine: An Ab Initio Study of the Structures and Gas-Phase Thermochemistry. J. Am. Chem. Soc 117 (1995) 1789-1796
12. Rauk A., Yu D., and Armstrong D.A. 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 (1997) 208-217
13. Block D.A., Yu D., Armstrong D.A., and Rauk A. On the Influence of Secondary Structure on the α-C-H Bond Dissociation Energy of Proline Residues in Proteins: A Theoretical Study. Can. J. Chem 76 (1998) 1042-1049
14. Rauk A., Yu D., Taylor J., Shustov G.V., Block D.A., and Armstrong D.A. Effects of Structure on α-C-H Bond Enthalpies of Amino Acid Residues: Relevance to H Transfers in Enzyme Mechanisms and in Protein Oxidation. Biochemistry 38 (1999) 9089-9096
15. Reid D.L., Armstrong D.A., Rauk A., and von Sonntag C. H-Atom Abstraction by Thiyl Radicals from Peptides and Cyclic Dipeptides. A Theoretical Study of Reaction Rates. Phys. Chem. Chem. Phys 5 (2003) 3994-3999
16. Chen X., and Tureček F. The Arginine Anomaly: Arginine Radicals Are Poor Hydrogen Atom Donors in Electron Transfer Induced Dissociations. J. Am. Chem. Soc 128 (2006) 12520-12530
17. Tureček F., Chen X., and Hao C. Where Does the Electron Go?. Electron Distribution and Reactivity of Peptide Cation Radicals Formed by Electron Transfer in the Gas Phase. J. Am. Chem. Soc 130 (2008) 8818-8833
18. Boltalina O.V., Hvelplund P., Jørgensen T.J.D., Larsen M.C., Larsson M.O., Sharoitchenko D.A., and Sørensen M. Electron Capture by Fluorinated Fullerene Anions in Collisions with Xe Atoms. Phys. Rev. A 62 (2000) 023202/1-7
19. Larsson M.O., Hvelplund P., Larsen M.C., Shen H., Cederquist H., and Schmidt H.T. Electron Capture and Energy Loss in ∼100 keV Collisions of Atomic and Molecular Ions on C60. Int. J. Mass Spectrom 177 (1998) 51-62
20. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B. 05 (2003), Gaussian, Inc, Pittsburgh PA
21. Becke A.D. A New Mixing of Hartree-Fock and Local Density-Functional Theories. J. Chem. Phys 98 (1993) 1372-1377
22. Becke A.D. Density Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys 98 (1993) 5648-5652
23. Rauhut G., and Pulay P. Transferable Scaling Factors for Density Functional Derived Vibrational Force Fields. J. Phys. Chem 99 (1995) 3093-3100
24. Møller C., and Plesset M.S. A Note on an Approximation Treatment for Many-Electron Systems. Phys. Rev 46 (1934) 618-622
25. Schlegel H.B. Potential Energy Curves Using Unrestricted Moller-Plesset Perturbation Theory with Spin Annihilation. J. Chem. Phys 84 (1986) 4530-4534
26. Mayer I. Spin-Projected UHF Method. IV. Comparison of Potential Curves Given by Different One-Electron Methods. Adv. Quantum. Chem 12 (1980) 189-262
27. + Ions. A Comparative G2(MP2) Ab Initio and Density Functional Theory Study. J. Phys. Chem. A 102 (1998) 4703-4713
28. Tureček F., and Wolken J.K. Dissociation Energies and Kinetics of Aminopyrimidinium Radicals by Ab Initio and Density Functional Theory. J. Phys. Chem. A 103 (1999) 1905-1912
29. Tureček F., Polášek M., Frank A.J., and Sadílek M. Transient Hydrogen Atom Adducts to Disulfides: Formation and Energetics. J. Am. Chem. Soc 122 (2000) 2361-2370
30. Polášek M., and Tureček F. Hydrogen Atom Adducts to Nitrobenzene. Formation of the Phenylnitronic Radical in the Gas Phase and Energetics of Wheland Intermediates. J. Am. Chem. Soc 122 (2000) 9511-9524
31. Rablen P.R. Is the Acetate Anion Stabilized by Resonance or Electrostatics?. A Systematic Structural Comparison. J. Am. Chem. Soc 122 (2000) 357-368
32. Rablen P.R. Computational Analysis of the Solvent Effect on the Barrier to Rotation about the Conjugated C-N Bond in Methyl N,N-Dimethylcarbamate. J. Org. Chem 65 (2000) 7930-7937
33. Rablen P.R., and Bentrup K.H. Are the Enolates of Amides and Esters Stabilized by Electrostatics?. J. Am. Chem. Soc 125 (2003) 2142-2147
34. Hirama M., Tokosumi T., Ishida T., and Aihara J. Possible Molecular Hydrogen Formation Mediated by the Inner and Outer Carbon Atoms of Typical PAH Cations. Chem. Phys 305 (2004) 307-316
35. Rassolov V.A., Ratner M.A., and Pople J.A. Electron Correlation in Chemical Bonds. J. Chem. Phys 112 (2000) 4014-4019
36. Stratmann R.E., Scuseria G.E., and Frisch M.J. An Efficient Implementation of Time-Dependent Density Functional Theory for the Calculation of Excitation Energies of Large Molecules. J. Chem. Phys 109 (1998) 8218-8224
37. Reed A.E., Weinstock R.B., and Weinhold F. Natural Population Analysis. J. Chem. Phys 83 (1985) 735-746
38. Gilbert R.G., and Smith S.C. Theory of Unimolecular and Recombination Reactions (1990), Blackwell Scientific Publications, Oxford, UK pp 52-132
39. Zhu L., and Hase W.L. General Program for Unimolecular Rate Constants (1994), Quantum Chemistry Program Exchange; Indiana University, Bloomington Program No. QCPE 644
40. Frank A.J., Sadílek M., Ferrier J.G., and Tureček F. Sulfur Oxyacids and Radicals in the Gas Phase. A Variable-Time Neutralization-Photoexcitation-Reionization Mass Spectrometric and Ab Initio/RRKM Study. J. Am. Chem. Soc 119 (1997) 12343-12353
41. Tureček F., and Syrstad E.A. Hydrogen Atom Adducts to the Amide Bond. Generation and Energetics of Amide Radicals in the Gas Phase. J. Am. Chem. Soc 125 (2003) 3353-3369
42. α Bond Dissociation Energies and Kinetics in Amide and Peptide Radicals. Is the Dissociation a Non-Ergodic Process?. J. Am. Chem. Soc 125 (2003) 5954-5963
43. Holm A.I.S., Hvelplund P., Kadhane U., Larsen M.K., Liu B., Nielsen S.B., Panja S., Pedersen J.M., Skrydstrup T., Støchkel K., Williams E.R., and Worm E.S. On the Mechanism of Electron-Capture-Induced Dissociation of Peptide Dications from 15N-Labeling and Crown-Ether Complexation. J. Phys. Chem. A 111 (2007) 9641-9643
44. Hvelplund P., Liu B., Nielsen S.B., Panja J.-C., Poully S., and Støchkel K. Electron Capture Induced Dissociation of Peptide Ions: Identification of Neutral Fragments from Secondary Collisions with Cesium Vapor. Int. J. Mass. Spectrom 263 (2007) 66-70
45. Hayakawa S., Hashimoto M., Matsubara H., and Turecek F. Dissecting the Proline Effect: Dissociations of Proline Radicals Formed by Electron Transfer to Protonated Pro-Gly and Gly-Pro Dipeptides in the Gas Phase. J. Am. Chem. Soc 129 (2007) 7936-7949
46. Harrison A.G. The Gas-Phase Basicities and Proton Affinities of Amino Acids and Peptides. Mass Spectrom. Rev 16 (1997) 201-217
47. Wolken J.K., and Tureček F. Modeling Nucleobase Radicals in the Gas Phase. Experimental and Computational Study of 2-Hydroxypyridinium and 2-(1H)Pyridone Radicals. J. Phys. Chem. A 103 (1999) 6268-6281
48. Tureček F. The Use of Kinetic Isotope Effects for the Determination of Internal Energy Distributions of Isolated Transient Species in the Gas Phase. Int. J. Mass Spectrom 227 (2003) 327-338
49. IUPAC Compendium of Chemical Technology. 2nd Ed. (1997). http://goldbook.iupac.org/C01480.html
50. Eliel E.L. Stereochemistry of Carbon Compounds (1962), McGraw-Hill, New York pp. 151-152, 237-38
51. Moran D., Jacob R., Wood G.P.F., Coote M.L., Davies M.J., O'Hair R.A.J., Easton C.J., and Radom L. Rearrangements in Model Peptide-Type Radicals via Intramolecular Hydrogen-Atom Transfer. Helv. Chim. Acta 89 (2006) 2254-2272
52. Chu I.K., Zhao J., Xu M., Siu S.O., Hopkinson A.C., and Siu K.W.M. Are the Radical Centers in Peptide Radical Cations Mobile?. The Generation, Tautomerism, and Dissociation of Isomeric α-Carbon-Centered Triglycine Radical Cations in the Gas Phase. J. Am. Chem. Soc 130 (2008) 7862-7872
53. Syrstad E.A., and Tureček F. Toward a General Mechanism of Electron-Capture Dissociation. J. Am. Soc. Mass Spectrom 16 (2005) 208-224
54. Sobczyk M., Anusiewicz I., Berdys-Kochanska J., Sawicka A., Skurski P., and Simons J. Coulomb-Assisted Dissociative Electron Attachment: Application to a Model Peptide. J. Phys. Chem. A 109 (2005) 250-258
55. Anusiewicz I., Berdys-Kochanska J., Skurski P., and Simons J. Simulating Electron Transfer Attachment to a Positively Charged Model Peptide. J. Phys. Chem. A 110 (2006) 1261-1266
56. Hayakawa S. Charge Inversion Mass Spectrometry: Dissociation of Resonantly Neutralized Molecules. J. Mass Spectrom 39 (2004) 111-135
57. n (n = 3-5) Neutrals Formed by Near-Resonant Neutralization Using Charge Inversion Mass Spectrometry. Eur. Phys. J. D 38 (2006) 163-176