Gas-phase doubly charged complexes of cyclic peptides with copper in +1, +2 and +3 formal oxidation states: Formation, structures and electron capture dissociation

Journal of Mass Spectrometry

Volumn 47, Issue 2, 2012, Pages 208-220

  Afonso, Carlos ^a   Tabet, Jean Claude ^a   Giorgi, Gianluca ^b   Tureček, František ^c  

^a Université Pierre et Marie Curie   (France)

^b UNIVERSITY OF SIENA   (Italy)

^c UNIVERSITY OF WASHINGTON   (United States)

Author keywords

copper peptide complexes; density functional theory; diastereoisomers; electron capture dissociation; recombination energies

Indexed keywords

COPPER-PEPTIDE COMPLEXES; DENSITY FUNCTIONALS; DIASTEREOISOMERS; ELECTRON CAPTURE DISSOCIATION; RECOMBINATION ENERGY;

AMIDES; COPPER; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRONIC STRUCTURE; ELECTRONS; HEAVY IONS; LIGANDS; OXIDATION; PEPTIDES; PROTONATION; PROTONS;

COPPER COMPOUNDS;

COPPER; COPPER COMPLEX; CUPRIC ION; CUPROUS ION; CYCLOPEPTIDE;

ARTICLE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; OXIDATION; PRIORITY JOURNAL; PROTON TRANSPORT;

COORDINATION COMPLEXES; COPPER; DEUTERIUM EXCHANGE MEASUREMENT; ELECTRONS; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 84857470765     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.2956     Document Type: Article

References (71)

1. K. D. Karlin, Z. Tyeklar,. Bioinorganic Chemistry of Copper. Chapman & Hall: New York, 1993.
2. W. Kaim, J. Rall,. Copper-A " Modern" Bioelement. Angew. Chem. Int. Ed Engl. 1996, 35, 43-60.
3. C. L. Gatlin, F. Tureček, T. Vaisar,. Copper(II) Amino Acid Complexes in the Gas Phase. J. Am. Chem. Soc. 1995, 117, 3637-3638.
4. +. J. Mass Spectrom. 1997, 32, 1037-1049.
5. 2. Int. J. Mass Spectrom. 1999, 192, 289-302.
6. M. H. Allen, T. W. Hutchens,. Electrospray-ionization Mass Spectrometry for the Detection of Discrete Peptide/Metal-ion Complexes Involving Multiple Cysteine (Sulfur) Ligands. Rapid Commun. Mass Spectrom. 1992, 6, 308-312.
7. 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. Anal. Chem. 1996, 68, 263-270.
8. C. Q. Jiao, B. S. Freiser, S. R. Carr, C. J. Cassady,. An Electrospray Ionmization Mass Spectrometry Study of Copper Adducts of Protonated Ubiquitin. J. Am. Soc. Mass Spectrom. 1995, 6, 521-524.
9. M. Lagarrigue, A. Bossee, C. Afonso, F. Fournier, B. Bellier, J. C. Tabet,. Diastereomeric differentiation of peptides with copper (II) and iron(II) complexation in an ion trap mass spectrometer. J. Mass Spectrom. 2006, 41, 1073-1085.
10. F. Fournier, C. Afonso, M. Menand, L. Hamon, J. Xie, J. C. Tabet,. Investigation by mass spectrometry of metal complexes of new molecular hosts: cyclic oligomer of sugar amino acid and sugar-aza-crown ethers. Eur. J. Mass Spectrom. 2008, 14, 61-69.
11. A. K. Y. Lam, B. F. Abrahams, M. J. Grannas, W. D. McFadyen, R. A. J. O'Hair,. Tuning the gas phase redox properties of copper(II) ternary complexes of terpyridines to control the formation of nucleobase radical cations. Dalton Trans. 2006, 5051-5061.
12. C. K. Barlow, B. D. M. Hodges, Y. Xia, R. A. J. O'Hair, S. A. McLuckey,. Gas-Phase Ion/Ion Reactions of Transition Metal Complex Cations with Multiply Charged Oligodeoxynucleotide Anions. J. Am. Soc. Mass Spectrom. 2008, 19, 281-293.
13. C. Afonso, A. Riu, Y. Xu, F. Fournier, J. C. Tabet,. Structural characterization of fatty acids cationized with copper by electrospray ionization mass spectrometry under low-energy collision-induced dissociation. J. Mass Spectrom. 2005, 40, 342-349.
14. F. Tureček,. Copper-biomolecule complexes in the gas phase. The ternary way. Mass Spectrom. Rev. 2007, 26, 563-582.
15. A. L. M. Lamsabhi, M. Yanez,. Gas-phase chemistry of organocopper compounds. Chemistry of Organocopper Compounds, Z. Rappoport, I. Marek, (Eds). Wiley: New York, 2009, (Pt. 1), 279-346.
16. J. Roithova, D. Schroeder,. Theory meets experiment: Gas-phase chemistry of coinage metals. Coordination Chem. Rev. 2009, 253, 666-677.
17. + peptide ions containing an N-terminal arginine. J. Am. Soc. Mass Spectrom. 2000, 11, 626-638.
18. + Ions. J. Am. Soc. Mass Spectrom. 2009, 20, 1263-1271.
19. D. Sanna, G. Micera, C. Kallay, V. Rigo, I. Sovago,. Copper (II) complexes of N-terminal protected tri- and tetra- peptides containing histidine residues. Dalton Trans. 2004, 2702-2707.
20. S. B. Shields, S. J. Franklin,. De Novo Design of a Copper (II)-Binding Helix-Turn-Helix Chimera: The Prion Octarepeat Motif in a New Context. Biochemistry 2004, 43, 16086-16091.
21. P. Kaczmarek, M. Jezowska-Bojczuk, K. Gatner, W. Bal,. Oxidative reactivity of Cu-TESHHK- and its alanine analogues. Dalton Trans. 2005, 1985-1988.
22. G. A. Rickard, R. Gomez-Balderas, P. Brunelle, D. F. Raffa, A. Rauk,. Binding Affinities for Models of Biologically Available Potential Cu(II) Ligands Relevant to Alzheimer's Disease: An ab Initio Study. J. Phys. Chem. A 2005, 109, 8361-8370.
23. G. Di Natale, G. Grasso, G. Impellizzeri, D. La Mendola, G. Micera, N. Mihala, Z. Nagy, K. Osz, G. Pappalardo, V. Rigo, E. Rizzarelli, D. Sanna, I. Sovago,. Copper (II) Interaction with Unstructured Prion Domain Outside the Octarepeat Region: Speciation, Stability, and Binding Details of Copper (II) Complexes with PrP106-126 Peptides. Inorg. Chem. 2005, 44, 7214-7225.
24. P. Stanczak, D. Valensin, P. Juszczyk, Z. Grzonka, C. Migliorini, E. Molteni, G. Valensin, E. Gaggelli, H. Kozlowski,. Structure and Stability of the CuII Complexes with Tandem Repeats of the Chicken Prion. Biochemistry 2005, 44, 12940-12954.
25. A. Jancso, Z. Paksi, N. Jakab, B. Gyurcsik, A. Rockenbauer, T. Gajda,. Solution chemical properties and catecholase-like activity of the copper (II)-Ac-His-His-Gly-His-OH system, a relevant functional model for copper containing oxidases. Dalton Trans. 2005, 3187-3194.
26. M. Tiliakos, E. Katsoulakou, A. Terzis, C. Raptopoulou, P. Cordopatis, E. Manessi-Zoupa,. The dipeptide H-Aib-L-Ala-OH ligand in copper (II) chemistry: Variation of product identity as a function of pH. Inorg. Chem. Commun. 2005, 8, 1085-1089.
27. A. J. Nicoll, D. J. Miller, K. Fuetterer, R. Ravelli, R. K. Allemann,. Designed High Affinity Cu2+-Binding α -Helical Foldamer. J. Am. Chem. Soc. 2006, 128, 9187-9193.
28. 2. Dalton Trans. 2006, 38, 4545-4552.
29. D. F. Raffa, A. Rauk,. Molecular Dynamics Study of the Beta Amyloid Peptide of Alzheimer's Disease and Its Divalent Copper Complexes. J. Phys. Chem. B 2007, 111, 3789-3799.
30. D. Jiang, L. Men, J. Wang, Y. Zhang, S. Chickenyen, Y. Wang, F. Zhou,. Redox Reactions of Copper Complexes Formed with Different β-Amyloid Peptides and Their Neuropathalogical Relevance. Biochemistry 2007, 46, 9270-9282.
31. N. I. Jakab, B. Gyurcsik, T. Koertvelyesi, I. Vosekalna, J. Jensen, E. Larsen,. Design of histidine containing peptides for better understanding of their coordination mode toward copper (II) by CD spectroscopy. J. Inorg. Biochem. 2007, 101, 1376-1385.
32. N. C. Maiti, D. Jiang, A. J. Wain, S. Patel, K. L. Dinh, F. Zhou,. Mechanistic Studies of Cu(II) Binding to Amyloid-β Peptides and the Fluorescence and Redox Behaviors of the Resulting Complexes. J. Phys. Chem. B 2008, 112, 8406-8411.
33. J. Brasun, A. Matera-Witkiewicz, S. Oldziej, A. Pratesi, M. Ginanneschi, L. Messori,. Impact of ring size on the copper (II) coordination abilities of cyclic tetrapeptides. J. Inorg. Biochem. 2009, 103, 813-817.
34. J. Brasun, A. Matera-Witkiewicz, E. Kamysz, W. Kamysz, S. Oldziej,. The influence of the cyclopeptide sequence on its coordination abilities towards Cu(II). Polyhedron 2010, 29, 1535-1542.
35. C. L. Gatlin, F. Tureček,. Electrospray Ionization of Inorganic and Organometallic Complexes. In Electrospray Ionization Mass Spectrometry, Fundamentals, Techniques, Applications, Cole R. B., (Ed). Wiley-Interscience: New York, 1997; Chapter 15, 527-570.
36. J. L. Seymour, F. Tureček,. Structure, Energetics, and Reactivity of Ternary Complexes of Amino Acids with Cu(II) and 2,2'-Bipyridine by Density Functional Theory. A Combination of Radical-Induced and Spin-Remote Fragmentations. J. Mass Spectrom. 2002, 37, 533-540.
37. 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. J. Mass Spectrom. 2001, 36, 306-316.
38. C. L. Gatlin, F. Tureček, T. Vaisar,. Determination of Soluble Cu(I) and Cu(II) Species in Jet Fuel by Electrospray Ionization Mass Spectrometry. Anal. Chem. 1994, 66, 3950-3958.
39. H. Lavanant, H. Virelizier, Y. Hoppilliard,. Reduction of copper(II) complexes by electron capture in an electrospray ionization source. J. Am. Soc. Mass Spectrom. 1998, 9, 1217-1221.
40. A. Tintaru, L. Charles, P. Milko, J. Roithova, D. Schroder,. Redox reactions of copper(II) upon electrospray ionization in the presence of acridine ligands with an amide side chain. J. Phys. Org. Chem. 2009, 22, 229-233.
41. T. Vaisar, J. W. Heinecke, J. L. Seymour, F. Turecek,. Copper-mediated intra-ligand oxygen transfer in gas-phase complexes with 3-nitrotyrosine. J. Mass Spectrom. 2005, 40, 608-614.
42. P. Wang,., G. Ohanessian, C. Wesdemiotis,. Cu(II)-catalyzed reactions in ternary [Cu(AA)(AA-H)]+complexes (AA = Gly, Ala, Val, Leu, Ile, t-Leu, Phe). Eur. J. Mass Spectrom. 2009, 15, 325-335.
43. T. Vaisar, C. L. Gatlin, F. Tureček,. Oxidation of Peptide-Copper Complexes by Alkali Metal Cations in the Gas Phase. J. Am. Chem. Soc. 1996, 118, 5314-5315.
44. T. Vaisar, C. L. Gatlin, F. Tureček,. Metal-Ligand Redox Reactions in Gas-Phase Quaternary Peptide-Metal Complexes by Electrospray Ionization Mass Spectrometry. Int. J. Mass Spectrom. Ion Processes 1997, 162, 77-87.
45. I. K. Chu, C. F. Rodriguez, T. C. Lau, A. C. Hopkinson, K. W. M. Siu,. Molecular radical cations of oligopeptides. J. Phys. Chem. B, 2000, 104, 3393-3397.
46. C. K. Barlow, S. Wee, W. D. McFadyen, R. A. J. O'Hair,. Designing copper(II) ternary complexes to generate radical cations of peptides in the gas phase: Role of the auxiliary ligand. Dalton Trans. 2004, 3199-3204.
47. C. K. Siu, Y. Ke, Y. Guo, A. C. Hopkinson, K. W. M. Siu,. Dissociations of copper(II)-containing complexes of aromatic amino acids: radical cations of tryptophan, tyrosine, a phenylalanine. Phys. Chem. Chem. Phys. 2008, 10, 5908-5918.
48. C. L. Gatlin, F. Tureček, T. Vaisar,. Gas-Phase Complexes of Amino Acids with Copper(II) and Diimine Ligands. Part II. Amino Acids with O, N and S Functional Groups in the Side-chain. J. Mass Spectrom. 1995, 30, 1617-1627.
49. A. Pratesi, P. Zanello, G. Giorgi, L. Messori, F. Laschi, A. Casini, M. Corsini, C. Gabbiani, M. Orfei, C. Rosani, M. Ginanneschi,. New Copper (II)/Cyclic Tetrapeptide System That Easily Oxidizes to Copper (III) under Atmospheric Oxygen. Inorg. Chem. 2007, 46, 10038-10040.
50. III) Complexes. J. Am. Soc. Mass Spectrom. 2007, 18, 791-801.
51. R. A. Zubarev, N. L. Kelleher, F. W. McLafferty,. Electron Capture Dissociation of Multiply Charged Protein Cations. A Nonergodic Process. J. Am. Chem. Soc. 1998, 120, 3265-3266.
52. 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 hormone oxytocin. Int. J Mass Spectrom. 2006, 253, 217-224.
53. F. Tureček, J. W. Jones, A. I. S. Holm, S. Panja, S. B. Nielsen, P. Hvelplund,. Transition Metals as Electron Traps. I. Structures, Energetics, Electron Capture, and Electron Transfer Dissociations of Ternary Copper-Peptide Complexes in the Gas Phase. J. Mass Spectrom. 2009, 44, 707-724.
54. F. Tureček, A. I. S. Holm, S. Panja, S. B. Nielsen, P. Hvelplund,. Transition Metals as Electron Traps. II. Structures, Energetics, Electron Capture, and Electron Transfer Dissociations of Ternary Co, Ni, and Zn-Peptide Complexes in the Gas Phase. J. Mass Spectrom. 2009, 44, 1518-1531.
55. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz,., J. Cioslowski, D. J. Fox,. Gaussian 09, Revision A.02, Gaussian, Inc.; Wallingford CT, 2009.
56. A. D. Becke,. New Mixing of Hartree-Fock and Local Density-Functional Theories. J. Chem. Phys. 1993, 98, 1372-1377.
57. A. D. Becke,. Density Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
58. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch,. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields. J. Phys. Chem. 1994, 98, 11623-11627.
59. P. J. Hay, W. R. Wadt,. Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms scandium to mercury. J. Chem. Phys. 1985, 82, 270.
60. P. J. Hay, W. R. Wadt,. Ab initio effective core potentials for molecular calculations. Potentials for potassium to gold including the outermost core orbitals. J. Chem. Phys. 1985, 82, 299.
61. Y. Zhao, D. G. Truhlar,. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Accounts 2008, 120, 215-241.
62. F. Furche, A. Ahlrichs,. Adiabatic time-dependent density functional methods for excited state properties. J. Chem. Phys., 2002, 117, 7433-7447.
63. A. E. Reed, R. B. Weinstock, F. Weinhold,. Natural population analysis. J. Chem. Phys. 1985, 83, 735-746.
64. F. Turecek,. The Use of Labeled Compounds. In: Applications of Mass Spectrometry to Organic Stereochemistry, Splitter J. S., Turecek, F., (Eds). VCH Publishers: New York, 1994, 676-677.
65. N. Leymarie, C. E. Costello, P. B. O'Connor,. Electron Capture Dissociation Intiates a Free Radical Reaction cascade. J. Am. Chem. Soc. 2003, 125, 8949-8958.
66. α Bond Dissociation Energies and Kinetics in Amide and Peptide Radicals. Is the Dissociation a Non-Ergodic Process? J. Am. Chem. Soc. 2003, 125, 5954-5963.
67. E. A. Syrstad, D. D. Stephens, F. Tureček,. Hydrogen Atom Adducts to the Amide Bond. Generation and Energetics of Amide Radicals in the Gas Phase. J. Phys. Chem. A 2003, 107, 115-126.
68. C. Yao, F. Tureček,. Hypervalent Ammonium Radicals. Competitive Nâ€"C and Nâ€"H Bond Dissociations in Methylammonium and Ethylammonium. Phys. Chem. Chem. Phys. 2005, 7, 912-920.
69. 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. J. Am. Chem. Soc. 2008, 130, 8818-8833.
70. F. Rogalewicz, Y. Hoppilliard, G. Ohanessian,. Structures and fragmentations of zinc(II) complexes of amino acids in the gas phase. I. Electrosprayed ions which are structurally different from their liquid phase precursors. Int. J. Mass Spectrom. 2000, 201, 307-320.
71. F. Rogalewicz, G. Louazel, Y. Hoppilliard, G. Ohanessian,. Structures and fragmentations of electrosprayed Zn(II) complexes of carboxylic acids in the gas phase Isomerisation versus desolvation during the last desolvation step. Int. J. Mass Spectrom. 2003, 228, 779-795.