Effects of transition metal ion coordination on the collision-induced dissociation of polyalanines

Journal of Mass Spectrometry

Volumn 46, Issue 11, 2011, Pages 1099-1107

  Watson, Heather M ^a   Vincent, John B ^a   Cassady, Carolyn J ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

CID; metal cationized peptide; peptide sequencing; polyalanine; transition metal

Indexed keywords

AMINO ACIDS; CHROMIUM COMPOUNDS; COBALT COMPOUNDS; DISSOCIATION; ELECTROSPRAY IONIZATION; IRON COMPOUNDS; MASS SPECTROMETRY; METAL IONS; NICKEL COMPOUNDS; PEPTIDES; PROTONATION; TRANSITION METALS;

CATIONIZED PEPTIDES; COLLISION INDUCED DISSOCIATION; FIRST ROW TRANSITION METALS; METAL ION INTERACTIONS; PEPTIDE SEQUENCING; POLYALANINE; QUADRUPOLE ION TRAPS; TANDEM MASS SPECTROMETRY;

COPPER COMPOUNDS;

ALANINE DERIVATIVE; AMINO ACID; CHROMIUM; COBALT; CUPRIC ION; CUPRIC OXIDE; FERRIC ION; FERROUS ION; METAL COMPLEX; METAL ION; NICKEL; POLYALANINE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

COLLISIONALLY ACTIVATED DISSOCIATION; ELECTROSPRAY; ION TRAP MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; SEQUENCE ANALYSIS; TANDEM MASS SPECTROMETRY;

EID: 82455205744     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1992     Document Type: Review

References (85)

1. E. I. Solomon, M. J. Baldwin, M. D. Lowery,. Electronic structures of active sites in copper proteins: contributions to reactivity. Chem. Rev. 1992, 92, 521.
2. I. Bertini, A. Sigel, H. Sigel, (Eds). 2001. Handbook on Metalloproteins. Marcel Dekker, Inc.: New York, NY, 2001.
3. J. A. Gutierrez, M. Wessling-Resnick,. Molecular mechanisms of iron transport. Crit. Rev. Eukaryot. Gene Expr. 1996, 6, 1.
4. J. B. Vincent,. The biochemistry of chromium. J. Nutr. 2000, 130, 715.
5. Z. Q. Wang, X. H. Zhang, J. C. Russell, M. Hulver, W. T. Cefalu,. Chromium picolinate enhances skeletal muscle cellular insulin signaling in vivo in obese, insulin-resistant JCR:LA-cp rats. J. Nutr. 2006, 136, 415.
6. H.-J. Thiesen, C. Bach,. Transition metals modulate DNA-protein interactions of SP1 zinc finger domains with its cognate target site. Biochem. Biophys. Res. Commun. 1991, 176, 551.
7. R. F. Service,. PROTEOMICS: new database to track protein locations. Science 2005, 309, 1310b.
8. M. Wilm, M. Mann,. Electrospray and Taylor-cone theory, Dole's beam of macromolecules at last? Int. J. Mass Spectrom. Ion Proc. 1994, 136, 167.
9. M. Wilm, M. Mann,. Analytical properties of the nanoelectrospray ion source. Anal. Chem. 1996, 68, 1.
10. R. Juraschek, T. Dülcks, M. Karas,. Nanoelectrospray - more than just a minimized-flow electrospray ionization source. J. Am. Soc. Mass Spectrom. 1999, 10, 300.
11. T. L. Constantopoulos, G. S. Jackson, C. G. Enke,. Effects of salt concentration on analyte response using electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 1999, 10, 625.
12. M. Karas, U. Bahr, T. Dülcks,. Nano-electrospray ionization mass spectrometry: addressing analytical problems beyond routine. Fresnius. J. Anal. Chem. 2000, 366, 669.
13. I. A. Papayannopoulos,. The interpretation of collision-induced dissociation tandem mass spectra of peptides. Mass Spectrom. Rev. 1995, 14, 49.
14. R. P. Grese, R. L. Cerny, M. L. Gross,. Metal ion-peptide interactions in the gas phase: a tandem mass spectrometry study of alkali metal cationized peptides. J. Am. Chem. Soc. 1989, 111, 2835.
15. T. Vaisar, C. L. Gatlin, F. Turecek,. Oxidation of peptide-copper complexes by alkali metal cations in the gas phase. J. Am. Chem. Soc. 1996, 118, 5314.
16. P. Hu, M. L. Gross,. Gas-phase interactions of transition-metal ions and di- and tripeptides: a comparison with alkaline-earth-metal-ion interactions. J. Am. Chem. Soc. 1993, 115, 8821.
17. 2+ by peptides: a direct reflection of aqueous-phase chemistry. J. Am. Chem. Soc. 1994, 116, 7827.
18. D. M. Crizer, Y. Xia, S. A. McLuckey,. Transition metal complex cations as reagents for gas-phase transformation of multiply deprotonated polypeptides. J. Am. Soc. Mass Spectrom. 2009, 20, 1718.
19. D. Pu, J. B. Vincent, C. J. Cassady,. The effects of chromium(III) coordination on the dissociation of acidic peptides. J. Mass Spectrom. 2008, 43, 773.
20. + cationized native and acetylated peptides. J. Mass Spectrom. 2002, 37, 910.
21. L. M. Teesch, J. Adams,. Metal ions as special reagents in analytical mass spectrometry. Org. Mass Spectrom. 1992, 27, 931.
22. L. M. Mallis, D. H. Russell,. Fast-atom-bombardment-tandem mass spectrometry studies of alkali-metal ions of small peptides. Anal. Chem. 1986, 58, 1076.
23. I. K. Chu, T. Shoeib, X. Guo, C. F. Rodriquez, T.-C. Lau, A. C. Hopkinson, K. W. M. Siu,. Characterization of the product ions from the collision-induced dissociation of argentinated peptides. J. Am. Soc. Mass Spectrom. 2001, 12, 163.
24. J. A. Loo,. Studying noncovalent protein complexes by electrospray ionization mass spectrometry. Mass Spectrom. Rev. 1997, 16, 1.
25. L. C. M. Ngoka, M. L. Gross,. Location of alkali metal binding sites in endothelin a selective receptor antagonists, cyclo(D-Trp-D-Asp-Pro-D-Val-Leu) and cyclo(D-Trp-D-Asp-Pro-D-Ile-Leu), from multistep collisionally activated decompositions. J. Mass Spectrom. 2000, 35, 265.
26. K. C. Barlow, R. A. J. O'Hair,. Gas-phase peptide fragmentation: how understanding the fundamentals provides a springboard to developing new chemistry and novel proteomic tools. J. Mass Spectrom. 2008, 43, 1301.
27. L. M. Teesch, J. Adams,. Fragmentations of gas-phase complexes between alkali metal ions and peptides: metal ion binding to carbonyl oxygens and other neutral functional groups. J. Am. Chem. Soc. 1991, 113, 812.
28. H. Sigel, R. B. Martin,. Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chem. Rev. 1982, 82, 385.
29. 2; an example of metal ion-promoted conformational organization which results in exceptionally high complex stability. J. Inorg. Biochem. 1993, 52, 79.
30. + peptide ions containing an N-terminal arginine. J. Am. Soc. Mass Spectrom. 2000, 11, 626.
31. +) with ketones and ethers. J. Am. Chem. Soc. 1981, 103, 4360.
32. P. B. Armentrout, L. F. Halle, J. L. Beauchamp,. Periodic trends in transition metal-hydrogen, metal-carbon, and metal-oxygen bond dissociation energies. Correlation with reactivity and electronic structure. J. Am. Chem. Soc. 1981, 103, 6501.
33. +. J. Am. Chem. Soc. 1976, 98, 5700.
34. + with nitroalkanes. J. Am. Chem. Soc. 1984, 106, 6125.
35. B. D. Radecki, J. Allison,. Parallels in the formation of transition metal-amide bonds in solution and in the gas phase: an ion cyclotron resonance study of cobalt ion chemistry with amines. J. Am. Chem. Soc. 1984, 106, 946.
36. S. J. Babinec, J. Allison,. The chemistry of first-row transition-metal ions with primary amines in the gas phase: correlations of reactivity with electronic structure. J. Am. Chem. Soc. 1984, 106, 7718.
37. J. Allison, R. B. Freas, D. P. Ridge,. Cleavage of alkanes by transition metal ions in the gas phase. J. Am. Chem. Soc. 1979, 101, 1332.
38. Z. Wu, F. A. Fernandez-Lima, D. H. Russell,. Amino acid influence on copper binding to peptides: Cysteine versus arginine. J. Am. Soc. Mass Spectrom. 2010, 21, 522.
39. 2+ with cysteine-containing peptides. J. Am. Soc. Mass Spectrom. 1998, 9, 1285.
40. P. Hu, C. Sorensen, M. L. Gross,. Influences of peptide side chains on the metal ion binding site in metal ion-cationized peptides: participation of aromatic rings in metal chelation. J. Am. Soc. Mass Spectrom. 1995, 6, 1079.
41. M. Kohtani, M. F. Jarrold, S. Wee, R. A. J. O'Hair,. Metal ion interactions with polyalanine peptides. J. Phys. Chem. B 2004, 108, 6093.
42. K. Cottingham,. Name that peptide. Anal. Chem. 2004, 76, 95A.
43. G. Lubec, L. Afjehi-Sadat,. Limitations and pitfalls in protein identification by mass spectrometry. Chem. Rev. 2007, 107, 3568.
44. J. Peng, J. E. Elias, C. C. Thoreen, L. J. Licklider, S. P. Gygi,. Evaluation of multidimensional chromatography coupled with tandem mass spectrometry (LC/LC-MS/MS) for large-scale protein analysis: the yeast proteome. J. Proteome Res. 2003, 2, 43.
45. D. L. Tabb, Y. Huang, V. H. Wysocki, J. R. Yates,. Influence of basic residue content on fragment ion peak intensities in low-energy collision-induceddissociation spectra of peptides. Anal. Chem. 2004, 76, 1243.
46. J. E. P. Syka, J. J. Coon, M. J. Schroeder, J. Shabanowitz, D. F. Hunt,. Peptide and protein sequence analysis by electron transfer dissociation mass spectrometry. Proc. Natl. Acad. Sci. 2004, 101, 9528.
47. B. Bogdanov, R. D. Smith,. Proteomics by FTICR mass spectrometry: top down and bottom up. Mass Spectrom. Rev. 2005, 24, 168.
48. A. R. Zubarev, N. A. Kruger, E. K. Fridriksson, M. A. Lewis, D. M. Horn, B. K. Carpenter, F. W. McLafferty,. Electron capture dissociation of gaseous multiply-charged proteins is favored at disulfide bonds and other sites of high hydrogen atom affinity. J. Am. Chem. Soc. 1999, 121, 2857.
49. 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.
50. A. L. McCormack, A. Somogyi, A. R. Dongre, V. H. Wysocki,. Fragmentation of protonated peptides: surface-induced dissociation in conjunction with a quantum mechanical approach. Anal. Chem. 1993, 65, 2859.
51. D. P. Little, J. P. Speir, M. W. Senko, P. B. O'Connor, F. W. McLafferty,. Infrared multiphoton dissociation of large multiply charged ions for biomolecule sequencing. Anal. Chem. 1994, 66, 2809.
52. R. Zubarev, A. Zubarev, M. Savitski,. Electron capture/transfer versus collisionally activated/induced dissociations: solo or duet? J. Am. Soc. Mass Spectrom. 2008, 19, 753.
53. R. E. Mesmer, C. F. Baes, Jr,. The Hydrolysis of Cations: A Critical Review of Hydrolytic Species and their Stability Constants in Aqueous Solution, Wiley-Interscience: New York, 1976.
54. Y. Eva Fung, H. Liu, T. Chan,. Electron capture dissociation of peptides metalated with alkaline-earth metal ions. J. Am. Soc. Mass Spectrom. 2006, 17, 757.
55. A. T. Iavarone, K. Paech, E. R. Williams,. Effects of charge state and cationizing agent on the electron capture dissociation of a peptide. Anal. Chem. 2004, 76, 2231.
56. 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.
57. H. Liu, K. HÃ¥kansson,. Electron capture dissociation of tyrosine O-sulfatedpeptides complexed with divalent metal cations. Anal. Chem. 2006, 78, 7570.
58. H. Liu, K. HÃ¥kansson,. Divalent metal ion-peptide interactions probed by electron capture dissociation of trications. J. Am. Soc. Mass Spectrom. 2006, 17, 1731.
59. Y. E. M. van der Burgt, M. Palmblad, H. Dalebout, R. M. A. Heeren, A. M. Deelder,. Electron capture dissociation of peptide hormone changes upon opening of the tocin ring and complexation with transition metal cations. Rapid Commun. Mass Spectrom. 2009, 23, 31.
60. W. Chan, P. White,. Fmoc Solid Phase Peptide Synthesis: A Practical Approach, Oxford University Press: New York, 2000.
61. J. Gao, Matrix-assisted Laser Desorption Ionization Time-of- flight Studies of Natural and Synthetic Peptides, PhD Dissertation, Department of Chemistry, The University of Alabama, Tuscaloosa, AL, 2008.
62. P. G. Wuts, T. W. Greene,. Greene's Protective Groups in Organic Synthesis, John Wiley & Sons, Inc.: Hoboken, NJ, 2006.
63. D. Kaplan, A. Brekenfeld, R. Hartmer, T. Ledertheil, C. Gebhardt, M. Schubert, Extending the capacity in modern spherical high capacity ion traps (HCT). Technical Note # TN-24: Bruker Daltonics, Billerica, MA, 2008.
64. P. Roepstorff, J. Fohlman,. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biol. Mass Spectrom. 1984, 11, 601.
65. 2+. Eur. Mass Spectrom. 1999, 5, 41.
66. A. E. Martell, R. M. Smith,. Critical Stability Constants, Vol. 1-6. Plenum Press: New York, 1974-1989.
67. C. Q. Jiao, B. S. Freiser, S. R. Carr, C. J. Cassady,. An electrospray ionization mass spectrometry study of copper adducts of protonated ubiquitin. J. Am. Soc. Mass Spectrom. 1995, 6, 521.
68. R. C. Burnier, G. D. Byrd, B. S. Freiser,. Copper (I) chemical ionization-mass spectrometric analysis of esters and ketones. Anal. Chem. 1980, 52, 1641.
69. 2+. J. Phys. Chem. A 2009, 113, 8883.
70. 2+-(glycyl)nglycine Complexes (n = 1-3). J. Phys. Chem. A 2008, 112, 3444.
71. J. S. Prell, T. G. Flick, J. Oomens, G. Berden, E. R. Williams,. Coordination of Trivalent Metal Cations to Peptides: results from IRMPD Spectroscopy and Theory. J. Phys. Chem. A 2009, 114, 854.
72. N. C. Polfer, J. Oomens, S. Suhai, B. Paizs,. Infrared spectroscopy and theoretical studies on gas-phase protonated Leu-enkephalin and its fragments: direct experimental evidence for the mobile proton. J. Am. Chem. Soc. 2007, 129, 5887.
73. N. C. Polfer, B. C. Bohrer, M. D. Plasencia, B. Paizs, D. E. Clemmer,. On the dynamics of fragment isomerization in collision-induced dissociation of peptides. J. Phys. Chem. A 2008, 112, 1286.
74. I. Riba-Garcia, K. Giles, R. H. Bateman, S. J. Gaskell,. Evidence for structural variants of a- and b-type peptide fragment ions using combined ion mobility/mass spectrometry. J. Am. Soc. Mass Spectrom. 2008, 19, 609.
75. n (n > = 3) ions in peptide spectra. J. Am. Soc. Mass Spectrom. 1996, 7, 233.
76. J. Yague, A. Paradela, M. Ramos, S. Ogueta, A. Marina, F. Barahona, J. Lopez de Castro, J. VÃzquez,. Peptide rearrangement during quadrupole ion trap fragmentation: added complexity to MS/MS spectra. Anal. Chem. 2003, 75, 1524.
77. + ions of protonated peptides. An ab initio study. Rapid Commun. Mass Spectrom. 2000, 14, 746.
78. T. Yalcin, C. Khouw, I. G. Csizmadia, M. R. Peterson, A. G. Harrison,. Why are b-ions stable species in peptide spectra? J. Am. Soc. Mass Spectrom. 1995, 6, 1165.
79. R. W. Vachet, B. M. Bishop, B. W. Erickson, G. L. Glish,. Novel peptide dissociation: gas-phase intramolecular rearrangement of internal amino acid residues. J. Am. Chem. Soc. 1997, 119, 5481.
80. V. W. M. Lee, H. Li, T.-C. Lau, K. W. M. Siu,. Structures of b and a Product Ions from the Fragmentation of Argentinated Peptides. J. Am. Chem. Soc. 1998, 120, 7302.
81. +-cationated α-amino acids. Rapid Commun. Mass Spectrom. 1995, 9, 1155.
82. +. J. Mass Spectrom. 1997, 32, 1037.
83. +1 with the 20 common amino acids. J. Am. Soc. Mass Spectrom. 1996, 7, 722.
84. 3* ions from protonated tetraglycine. J. Am. Soc. Mass Spectrom. 2006, 17, 1654.
85. B. J. Bythell, D. F. Barofsky, F. Pingitore, M. J. Polce, P. Wang, C. Wesdemiotis, B. Paizs,. Backbone cleavages and sequential loss of carbon monoxide and ammonia from protonated AGG: a combined tandem mass spectrometry, isotope labeling, and theoretical study. J. Am. Soc. Mass Spectrom. 2007, 18, 1291.