Tandem mass spectrometry (MSn) of peptide disulfide regio-isomers via collision-induced dissociation: Utility and limits in disulfide bond characterization

International Journal of Mass Spectrometry

Volumn 343-344, Issue , 2013, Pages 50-57

  Durand, Kirt L ^a   Ma, Xiaoxiao ^a   Plummer, Chelsea E ^a,b   Xia, Yu ^a  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

Collision induced dissociation (CID); Disulfide linkage determination; Disulfide regio isomer; Peptide fragmentation; Tandem mass spectrometry (MSn)

Indexed keywords

EID: 84877924131     PISSN: 13873806     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijms.2013.04.005     Document Type: Article

References (46)

1. J.M. Thornton Disulphide bridges in globular proteins Journal of Molecular Biology 151 1981 261 287
2. M. Nakazato, H. Yamaguchi, H. Kinoshita, K. Kangawa, H. Matsuo, N. Chino, and S. Matsukura Identification of biologically active and inactive human uroguanylins in plasma and urine and their increases in renal insufficiency Biochemical and Biophysical Research Communications 220 1996 586 593
3. H. Yano, S. Kuroda, and B.B. Buchanan Disulfide proteome in the analysis of protein function and structure Journal of Proteomics 2 2002 1090 1096
4. J.J. Gorman, T.P. Wallis, and J.J. Pitt Protein disulfide bond determination by mass spectrometry Mass Spectrometry Reviews 21 2002 183 216
5. H.Y. Tang, and D.W. Speicher Determination of disulfide-bond linkages in proteins Current Protocols in Protein Science 2004 John Wiley & Sons, Inc. Hoboken, NJ 11.11.1 11.11.20 (Chapter 11, Unit 11.11)
6. Y. Zhang, H.D. Dewald, and H. Chen Online mass spectrometric analysis of proteins/peptides following electrolytic cleavage of disulfide bonds Journal of Proteome Research 10 2011 1293 1304
7. Y. Zhang, W. Cui, H. Zhang, H.D. Dewald, and H. Chen Electrochemistry- assisted top-down characterization of disulfide-containing proteins Analytical Chemistry 84 2012 3838 3842
8. S.L. Wu, H. Jiang, W.S. Hancock, and B.L. Karger Identification of the unpaired cysteine status and complete mapping of the 17 disulfides of recombinant tissue plasminogen activator using LC-MS with electron transfer dissociation/collision induced dissociation Analytical Chemistry 82 2010 5296 5303
9. F. Sanger A disulphide interchange reaction Nature 171 1953 1025 1026
10. J.M. Chong, A. Uren, J.S. Rubin, and D.W. Speicher Disulfide bond assignments of secreted Frizzled-related protein-1 provide insights about Frizzled homology and netrin modules Journal of Biological Chemistry 277 2002 5134 5144
11. D.F. Clark, E.P. Go, M.L. Toumi, and H. Desaire Collision induced dissociation products of disulfide-bonded peptides: ions result from the cleavage of more than one bond Journal of the American Society for Mass Spectrometry 22 2011 492 498
12. H. Lioe, and R.A. O'Hair A novel salt bridge mechanism highlights the need for nonmobile proton conditions to promote disulfide bond cleavage in protonated peptides under low-energy collisional activation The American Society for Mass Spectrometry 18 2007 1109 1123
13. P.A. Chrisman, and S.A. McLuckey Dissociations of disulfide-linked gaseous polypeptide/protein anions: ion chemistry with implications for protein identification and characterization Journal of Proteome Research 1 2002 549 557
14. 2S from Cys. A joint experimental and theoretical study Rapid Communications in Mass Spectrometry 17 2003 2488 2494
15. D. Bilusich, C.S. Brinkworth, and J.H. Bowie Negative ion mass spectra of Cys-containing peptides. The characteristic Cys gamma backbone cleavage: a joint experimental and theoretical study Rapid Communications in Mass Spectrometry 18 2004 544 552
16. D. Bilusich, V.M. Maselli, C.S. Brinkworth, T. Samguina, A.T. Lebedev, and J.H. Bowie Direct identification of intramolecular disulfide links in peptides using negative ion electrospray mass spectra of underivatised peptides. A joint experimental and theoretical study Rapid Communications in Mass Spectrometry 19 2005 3063 3074
17. D. Bilusich, and J.H. Bowie Identification of intermolecular disulfide linkages in underivatised peptides using negative ion electrospray mass spectrometry. A joint experimental and theoretical study Rapid Communications in Mass Spectrometry 21 2007 619 628
18. S.S. Thakur, and P. Balaram Fragmentation of peptide disulfides under conditions of negative ion mass spectrometry: studies of oxidized glutathione and contryphan Journal of the American Society for Mass Spectrometry 19 2008 358 366
19. A. Agarwal, J.K. Diedrich, and R.R. Julian Direct elucidation of disulfide bond partners using ultraviolet photodissociation mass spectrometry Analytical Chemistry 83 2011 6455 6458
20. N.P. Ewing, and C.J. Cassady Dissociation of multiply charged negative ions for hirudin (54-65), fibrinopeptide B, and insulin A (oxidized) Journal of the American Society for Mass Spectrometry 12 2001 105 116
21. M.F. Bean, and S.A. Carr Characterization of disulfide bond position in proteins and sequence analysis of cystine-bridged peptides by tandem mass spectrometry Analytical Biochemistry 201 1992 216 226
22. H. Lioe, M. Duan, and R.A. O'Hair Can metal ions be used as gas-phase disulfide bond cleavage reagents? A survey of coinage metal complexes of model peptides containing an intermolecular disulfide bond Rapid Communications in Mass Spectrometry 21 2007 2727 2733
23. H.I. Kim, and J.L. Beauchamp Mapping disulfide bonds in insulin with the Route 66 Method: selective cleavage of SC bonds using alkali and alkaline earth metal enolate complexes Journal of the American Society for Mass Spectrometry 20 2009 157 166
24. H.I. Kim, and J.L. Beauchamp Identifying the presence of a disulfide linkage in peptides by the selective elimination of hydrogen disulfide from collisionally activated alkali and alkaline earth metal complexes Journal of the American Chemical Society 130 2008 1245 1257
25. H.P. Gunawardena, R.A. O'Hair, and S.A. McLuckey Selective disulfide bond cleavage in gold(I) cationized polypeptide ions formed via gas-phase ion/ion cation switching Journal of Proteome Research 5 2006 2087 2092
26. A.J. Kleinnijenhuis, R. Mihalca, R.M.A. Heeren, and A.J.R. Heck Atypical behavior in the electron capture induced dissociation of biologically relevant transition metal ion complexes of the peptide hormone oxytocin International Journal of Mass Spectrometry 253 2006 217 224
27. R. Mihalca, Y.E. van der Burgt, A.J. Heck, and R.M. Heeren Disulfide bond cleavages observed in SORI-CID of three nonapeptides complexed with divalent transition-metal cations Journal of Mass Spectrometry 42 2007 450 458
28. D. Liu, A.B. Seuthe, O.T. Ehrler, X. Zhang, T. Wyttenbach, J.F. Hsu, and M.T. Bowers Oxytocin-receptor binding: why divalent metals are essential Journal of the American Chemical Society 127 2005 2024 2025
29. L.M. Teesch, R.C. Orlando, and J. Adams Location of the alkali metal ion in gas-phase peptide complexes Journal of the American Chemical Society 113 1991 3668 3675
30. M. Mentinova, and S.A. McLuckey Cleavage of multiple disulfide bonds in insulin via gold cationization and collision-induced dissociation International Journal of Mass Spectrometry 308 2011 133 136
31. M.D. Jones, S.D. Patterson, and H.S. Lu Determination of disulfide bonds in highly bridged disulfide-linked peptides by matrix-assisted laser desorption/ionization mass spectrometry with postsource decay Analytical Chemistry 70 1998 136 143
32. S.R. Cole, X. Ma, X. Zhang, and Y. Xia Electron transfer dissociation (ETD) of peptides containing intrachain disulfide bonds Journal of the American Society for Mass Spectrometry 23 2012 310 320
33. R.A. Zubarev, D.M. Horn, E.K. Fridriksson, N.L. Kelleher, N.A. Kruger, M.A. Lewis, B.K. Carpenter, and F.W. McLafferty Electron capture dissociation for structural characterization of multiply charged protein cations Analytical Chemistry 72 2000 563 573
34. A. Kalli, and K. Hakansson Preferential cleavage of SS and CS bonds in electron detachment dissociation and infrared multiphoton dissociation of disulfide-linked peptide anions International Journal of Mass Spectrometry 263 2007 71 81
35. Y.M.E. Fung, F. Kjeldsen, O.A. Silivra, T.W.D. Chan, and R.A. Zubarev Facile disulfide bond cleavage in gaseous peptide and protein cations by ultraviolet photodissociation at 157 nm Angewandte Chemie 117 2005 6557 6561
36. Y. Xia, and R.G. Cooks Plasma induced oxidative cleavage of disulfide bonds in polypeptides during nanoelectrospray ionization Analytical Chemistry 82 2010 2856 2864
37. X. Ma, C.B. Love, X. Zhang, and Y. Xia Gas-phase fragmentation of [M+nH+OH]n+ ions formed from peptides containing intra-molecular disulfide bonds Journal of the American Society for Mass Spectrometry 22 2011 922 930
38. L.P. Renaud, and C.W. Bourque Neurophysiology and neuropharmacology of hypothalamic magnocellular neurons secreting vasopressin and oxytocin Progress in Neurobiology 36 1991 131 169
39. R.I. Lehrer, and T. Ganz Antimicrobial peptides in mammalian and insect host defence Current Opinions in Immunology 11 1999 23 27
40. L. Narasimhan, J. Singh, C. Humblet, K. Guruprasad, and T. Blundell Snail and spider toxins share a similar tertiary structure and 'cystine motif' Nature Structure and Molecular Biology 12 1994 850 852
41. V. Badock, M. Raida, K. Adermann, W.G. Forssmann, and M. Schrader Distinction between the three disulfide isomers of guanylin 99-115 by low-energy collision-induced dissociation Rapid Communications in Mass Spectrometry 12 1998 1952 1956
42. K. Gupta, M. Kumar, and P. Balaram Disulfide bond assignments by mass spectrometry of native natural peptides: cysteine pairing in disulfide bonded conotoxins Analytical Chemistry 82 2010 8313 8319
43. L.F. Heneghan, and J.C. Bailar The stereoisomerism of complex inorganic compounds. XVI. The stereoisomers of dichlorobis-(ethylenediamine)-platinum(IV) salts Journal of the American Chemical Society 75 1953 1840 1841
44. S.J. Bark, N. Muster, J.R. Yates 3rd, and G. Siuzdak High-temperature protein mass mapping using a thermophilic protease Journal of the American Chemical Society 123 2001 1774 1775
45. M. Wilm, and M. Mann Analytical properties of the nanoelectrospray ion source Analytical Chemistry 68 1996 1 8
46. M. Mormann, J. Eble, C. Schwoppe, R.M. Mesters, W.E. Berdel, J. Peter-Katalinic, and G. Pohlentz Fragmentation of intra-peptide and inter-peptide disulfide bonds of proteolytic peptides by nanoESI collision-induced dissociation Analytical and Bioanalytical Chemistry 392 2008 831 838