Spectroscopic evidence for an oxazolone structure in anionic b-type peptide fragments

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 2, 2012, Pages 290-300

  Grzetic, Josipa ^a   Oomens, Jos ^a,b  

^a FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

b type ion; deprotonated peptides; ion structure; IRMPD spectroscopy; peptide fragmentation

Indexed keywords

COLLISION INDUCED DISSOCIATION; CONJUGATED STRUCTURES; DIKETOPIPERAZINES; GAS-PHASE STABILITY; INFRARED SPECTRUM; ION STRUCTURE; IR SPECTRUM; IRMPD SPECTROSCOPY; ISOMERIC STRUCTURES; MULTIPLE-PHOTON DISSOCIATION; NEGATIVE CHARGE; OXAZOLONE RING; PEPTIDE FRAGMENTATION; PEPTIDE FRAGMENTS; SPECTRAL RANGE; SPECTROSCOPIC EVIDENCE; STRUCTURAL CHARACTERIZATION;

DENSITY FUNCTIONAL THEORY; DISSOCIATION; FREE ELECTRON LASERS; ISOMERS; ORGANIC POLYMERS; PHASE STABILITY; SPECTROMETERS; SPECTROSCOPY;

PEPTIDES;

ALANINE DERIVATIVE; ALANYLTYROSILALANINE; OXAZOLONE; PIPERAZINEDIONE; TRIALANINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; CONJUGATION; CONTROLLED STUDY; ENERGY TRANSFER; FREE ELECTRON LASER; GAS; INFRARED SPECTROSCOPY; LASER; OPTICAL DENSITY; PEPTIDE ANALYSIS; PROTEIN STABILITY; PROTEIN STRUCTURE; PROTON TRANSPORT; STRUCTURE ANALYSIS; SURFACE CHARGE;

ANIONS; MASS SPECTROMETRY; OXAZOLONE; PEPTIDE FRAGMENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84856244936     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0297-3     Document Type: Article

References (56)

1. McLafferty, F. W. Tandem Mass Spectrometry (MS/MS): A Promising New Analytical Technique for Specific Component Determination in Complex Mixtures. Acc. Chem. Res. 13, 33-39 (1980)
2. G Siuzdak 1994 The Emergence of Mass-Spectrometry in Biochemical-Research Proc. Nat. Acad. Sci. U.S.A. 91 11290 11297 10.1073/pnas.91.24.11290 1:CAS:528:DyaK2MXitlyku7o%3D (Pubitemid 24356330)
3. Jr. Yates 1998 Mass Spectrometry and the Age of the Proteome J. Mass Spectrom. 33 1 19 10.1002/(SICI)1096-9888(199801)33:1<1::AID-JMS624>3.0. CO;2-9 1:CAS:528:DyaK1cXnsFSgtA%3D%3D (Pubitemid 28034055)
4. K Biemann 1988 Contributions of Mass Spectrometry to Peptide and Protein Structure Biol. Mass Spectrom. 16 99 111 10.1002/bms.1200160119 1:STN:280:DyaL1M3gslyqtg%3D%3D (Pubitemid 18265782)
5. 5 Ions. J. Am. Soc. Mass Spectrom. 19, 1776-1780 (2008)
6. C Bleiholder S Osburn TD Williams S Suhai M Van Stipdonk AG Harrison B Paizs 2008 Sequence-Scrambling Fragmentation Pathways of Protonated Peptides J. Am. Chem. Soc. 130 17774 17789 10.1021/ja805074d 1:CAS:528:DC%2BD1cXhsVOjsLnI
7. L Yu Y Tan Y Tsai DR Goodlett NC Polfer 2011 On the Relevance of Peptide Sequence Permutations in Shotgun Proteomics Studies J. Proteome Res. 10 2409 2416 10.1021/pr101235w 1:CAS:528:DC%2BC3MXkt1Wnsb0%3D
8. NC Polfer J Oomens S Suhai B Paizs 2005 Spectroscopic and Theoretical Evidence for Oxazolone Ring Formation in Collision-Induced Dissociation of Peptides J. Am. Chem. Soc. 127 17154 17155 10.1021/ja056553x 1:CAS:528:DC%2BD2MXht1WitbvM (Pubitemid 41791013)
9. NC Polfer J Oomens S Suhai B Paizs 2007 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. 129 5887 5897 10.1021/ja068014d 1:CAS:528:DC%2BD2sXktFegs7o%3D (Pubitemid 46748493)
10. MM Savitski M Falth YME Fung CM Adams RA Zubarev 2008 Bifurcating Fragmentation Behavior of Gas-Phase Tryptic Peptide Dications in Collisional Activation J. Am. Soc. Mass Spectrom. 19 1755 1763 10.1016/j.jasms.2008.08.003 1:CAS:528:DC%2BD1cXhsVyrtrjO
11. 2 Fragment Ion from Protonated Tri-Alanine J. Am. Soc. Mass Spectrom. 20 334 339 10.1016/j.jasms.2008.10.012 1:CAS:528:DC%2BD1MXhtFyqtrw%3D
12. + Ion J. Am. Chem. Soc. 130 17644 17645 10.1021/ja8067929 1:CAS:528:DC%2BD1cXhsVOmt77F
13. + Ion J. Am. Chem. Soc. 131 17528 17529 10.1021/ja9054542 1:CAS:528:DC%2BD1MXhtl2qtbbN
14. S Molesworth S Osburn M Van Stipdonk 2009 Influence of Size on Apparent Scrambling of Sequence During CID of b-Type Ions J. Am. Soc. Mass Spectrom. 20 2174 2181 10.1016/j.jasms.2009.07.023 1:CAS:528:DC%2BD1MXht1ylsbrM
15. 5 Ions J. Am. Soc. Mass Spectrom. 21 1028 1036 10.1016/j.jasms.2010.02.011 1:CAS:528: DC%2BC3cXmt1ensbs%3D
16. 8 J. Am. Chem. Soc. 131 18272 18282 10.1021/ja9030837 1:CAS:528:DC%2BD1MXhsV2hurvM
17. 4: Insights from Infrared Multiple-Photon Dissociation Spectroscopy and Gas-Phase Hydrogen/Deuterium Exchange. J. Am. Soc. Mass Spectrom. 21, 1313-1321 (2010)
18. U Erlekam BJ Bythell D Scuderi M Van Stipdonk B Paizs PJ Maitre 2009 Am. Chem. Soc. 131 11503 10.1021/ja903390r 1:CAS:528:DC%2BD1MXptFChsL8%3D
19. 2 Ion Derived from Triglycine: An N1-Protonated 4-Imidazolidinone J. Phys. Chem. Lett. 1 868 872 10.1021/jz900464a 1:CAS:528:DC%2BC3cXhvFWgtLs%3D
20. n Fragment Ions of Protonated Peptides J. Am. Chem. Soc. 132 14766 14779 10.1021/ja101556g 1:CAS:528:DC%2BC3cXht1GqtrjN
21. - Fragment Anion by IR Spectroscopy J. Am. Soc. Mass Spectrom. 21 698 706 10.1016/j.jasms.2010.01.004 1:CAS:528:DC%2BC3cXks1GksLo%3D
22. 2 Ions Derived from Deprotonated Dipeptides-a Synergy between Experiment and Theory J. Phys. Chem. A 106 9695 9704 10.1021/jp0208891 1:CAS:528:DC%2BD38XlvFGls74%3D (Pubitemid 35410139)
23. W Kulik W Heerma 1989 Fast Atom Bombardment Tandem Mass-Spectrometry for Amino-Acid Sequence Determination in Tripeptides Biomed. Environm. Mass Spectrom. 18 910 917 10.1002/bms.1200181011 1:CAS:528:DyaK3cXktVKkurw%3D (Pubitemid 19244208)
24. D Vansetten W Kulik W Heerma 1990 Isomeric Tripeptides-a Study on Structure Spectrum Relationship Biomed. Environ. Mass Spectrom. 19 475 480 10.1002/bms.1200190805 1:CAS:528:DyaK3cXmtlajsLk%3D (Pubitemid 20273435)
25. N Bache KD Rand P Roepstorff M Ploug TJD Jørgensen 2008 Hydrogen Atom Scrambling in Selectively Labeled Anionic Peptides Upon Collisional Activation by MALDI Tandem Time-of-Flight Mass Spectrometry J. Am. Soc. Mass Spectrom. 19 1719 1725 10.1016/j.jasms.2008.05.021 1:CAS:528:DC%2BD1cXhsVyrtrvF
26. RJ Waugh JH Bowie 1994 A Review of the Collision-Induced Dissociations of Deprotonated Dipeptides and Tripeptides-an Aid to Structure Determination Rapid Commun. Mass Spectrom. 8 169 173 10.1002/rcm.1290080209 1:CAS:528: DyaK2cXisVGksr4%3D (Pubitemid 2046121)
27. - Parent Anions of Underivatized Peptides: An Aid to Structure Determination and Some Unusual Negative Ion Cleavages Mass Spectrom. Rev. 21 87 107 10.1002/mas.10022 1:CAS:528:DC%2BD38XovFWru7w%3D (Pubitemid 35355219)
28. M Eckersley JH Bowie RN Hayes 1989 Collision-Induced Dissociations of Deprotonated Peptides, Dipeptides and Tripeptides with Hydrogen and Alkyl -Groups-an Aid to Structure Determination Org. Mass Spectrom. 24 597 602 10.1002/oms.1210240814 1:CAS:528:DyaK3cXhsFyqtro%3D
29. 2 Ions. Rapid Commun. Mass Spectrom. 17, 869-875 (2003) (Pubitemid 36433173)
30. A Harrison A Young 2004 Fragmentation of Deprotonated N-Benzoylpeptides: Formation of Deprotonated Oxazolones J. Am. Soc. Mass Spectrom. 15 446 456 10.1016/j.jasms.2003.11.018 1:CAS:528:DC%2BD2cXisVGhur4%3D (Pubitemid 38407130)
31. AG Harrison 2001 Sequence-Specific Fragmentation of Deprotonated Peptides Containing H or Alkyl Side Chains J. Am. Soc. Mass Spectrom. 12 1 13 10.1016/S1044-0305(00)00199-9 1:CAS:528:DC%2BD3cXovFWhsbs%3D (Pubitemid 34546641)
32. AG Harrison AB Young 2005 Fragmentation Reactions of Deprotonated Peptides Containing Proline The Proline Effect. J. Mass Spectrom. 40 1173 1186 1:CAS:528:DC%2BD2MXhtVGmu73E (Pubitemid 41337245)
33. 2 Ions Derived from Deprotonated Peptides. A Comparison of Method and Basis Set Used on Relative Product Stabilities J. Mol. Struct. Theochem. 675 149 162 10.1016/j.theochem.2003.12.040 1:CAS:528:DC%2BD2cXjsl2mtbk%3D
34. D Oepts AFG van der Meer PW van Amersfoort 1995 The Free-Electron-Laser User Facility FELIX Infrared Phys. Technol. 36 297 308 10.1016/1350-4495(94) 00074-U 1:CAS:528:DyaK2MXltlCksrg%3D
35. Polfer, N. C.; Oomens, J. Reaction Products in Mass Spectrometry Elucidated with Infrared Spectroscopy. Phys. Chem.; Chem. Phys. 9, 3804-3817 (2007)
36. JJ Valle Jr. Eyler J Oomens DT Moore AFG van der Meer G von Helden G Meijer CL Hendrickson AG Marshall GT Blakney 2005 Free Electron Laser-Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Facility for Obtaining Infrared Multiphoton Dissociation Spectra of Gaseous Ions Rev. Sci. Instrum. 76 7 10.1063/1.1841953 (Pubitemid 40238174)
37. TH Mize I Taban M Duursma M Seynen M Konijnenburg A Vijftigschild CV Doornik GV Rooij RMA Heeren 2004 A Modular Data and Control System to Improve Sensitivity, Selectivity, Speed of Analysis, Ease of Use, and Transient Duration in an External Source FTICR-MS Int. J. Mass Spectrom. 235 243 253 10.1016/j.ijms.2004.05.003 1:CAS:528:DC%2BD2cXlvFCqsL8%3D
38. AG Marshall TCL Wang TL Ricca 1985 Tailored Excitation for Fourier Transform Ion Cyclotron Mass Spectrometry J. Am. Chem. Soc. 107 7893 7897 10.1021/ja00312a015 1:CAS:528:DyaL28Xht1KisA%3D%3D
39. J Oomens BG Sartakov G Meijer G von Helden 2006 Gas-Phase Infrared Multiple Photon Dissociation Spectroscopy of Mass-Selected Molecular Ions Int. J. Mass Spectrom. 254 1 19 10.1016/j.ijms.2006.05.009 1:CAS:528: DC%2BD28XmslGqtbg%3D
40. NC Polfer J Oomens 2009 Vibrational Spectroscopy of Bare and Solvated Ionic Complexes of Biological Relevance Mass Spectrom. Rev. 28 468 494 10.1002/mas.20215 1:CAS:528:DC%2BD1MXmtVSksrw%3D
41. N Polfer 2011 Infrared Multiple Photon Dissociation Spectroscopy of Trapped Ions Chem. Soc. Rev. 40 2211 2221 10.1039/c0cs00171f 1:CAS:528:DC%2BC3MXkvVWju7s%3D
42. L MacAleese P Maitre 2007 Infrared Spectroscopy of Organometallic Ions in the Gas Phase: From Model to Real World Complexes Mass Spectrom. Rev. 26 583 605 10.1002/mas.20138 1:CAS:528:DC%2BD2sXot1KltLg%3D (Pubitemid 47169780)
43. GN Merrill SR Kass 1996 Calculated Gas-Phase Acidities Using Density Functional Theory: Is It Reliable? J. Phys. Chem. 100 17465 17471 10.1021/jp961557x 1:CAS:528:DyaK28XmtFKgurs%3D (Pubitemid 126787072)
44. JD Steill J Oomens 2009 Action Spectroscopy of Gas-Phase Carboxylate Anions by Multiple Photon Ir Electron Detachment/Attachment J. Phys. Chem. A 113 4941 4946 10.1021/jp807710y 1:CAS:528:DC%2BD1MXjvF2hu70%3D
45. PA Wabnitz RJ Waugh MA Eckersley S Dua T Blumenthal JH Bowie 1996 The Negative Ion Mass Spectra of Deprotonated 2,5-Diketopiperazines Int. J. Mass Spectrom. Ion Processes 154 193 201 10.1016/0168-1176(96)04378-9 1:CAS:528:DyaK28Xkt12qtbY%3D (Pubitemid 126740022)
46. RJ Waugh JH Bowie RN Hayes 1991 Collision Induced Dissociations of Deprotonated Peptides: Dipeptides Containing Phenylalanine, Tyrosine. Histidine and Tryptophan Int. J. Mass Spectrom. Ion Processes 107 333 347 10.1016/0168-1176(91)80068-X 1:CAS:528:DyaK3MXlsF2kt7o%3D
47. CM Jones M Bernier E Carson KE Colyer R Metz A Pawlow ED Wischow I Webb EJ Andriole JC Poutsma 2007 Gas-Phase Acidities of the 20 Protein Amino Acids Int. J. Mass Spectrom. 267 54 62 10.1016/j.ijms.2007.02.018 1:CAS:528: DC%2BD2sXhtFShs7fN
48. Z Tian X-B Wang L-S Wang SR Kass 2009 Are Carboxyl Groups the Most Acidic Sites in Amino Acids? Gas-Phase Acidities, Photoelectron Spectra, and Computations on Tyrosine, p-Hydroxybenzoic Acid, and Their Conjugate Bases J. Am. Chem. Soc. 131 1174 1181 10.1021/ja807982k 1:CAS:528:DC%2BD1MXnt1Gg
49. J Oomens JD Steill B Redlich 2009 Gas-Phase IR Spectroscopy of Deprotonated Amino Acids J. Am. Chem. Soc. 131 4310 4319 10.1021/ja807615v 1:CAS:528:DC%2BD1MXislOjtb0%3D
50. WE Sinclair DW Pratt 1996 Structure and Vibrational Dynamics of Aniline and Aniline-Ar from High Resolution Electronic Spectroscopy in the Gas Phase J. Chem. Phys. 105 15 10.1063/1.472710
51. Piest, H.; Helden, v. G.; Meijer, G. Infrared Spectroscopy of Jet-Cooled Neutral and Ionized Aniline-Ar. J. Chem. Phys. 110, 2010-2015 (1999) (Pubitemid 129615044)
52. Paizs, B.; Suhai, S. Towards Understanding the Tandem Mass Spectra of Protonated Oligopeptides. 1: Mechanism of Amide Bond Cleavage. J. Am. Soc. Mass Spectrom. 15, 103-113 (2004) (Pubitemid 38091672)
53. 2 Ions. Rapid Commun. Mass Spectrom. 16, 375-389 (2002) (Pubitemid 34174675)
54. + Ions from Protonated Peptides: An Ab Initio Study Rapid Commun. Mass Spectrom. 13 525 533 10.1002/(SICI)1097-0231(19990330)13:6<525::AID- RCM519>3.0.CO;2-O 1:CAS:528:DyaK1MXitVSju7Y%3D (Pubitemid 29139215)
55. + J. Am. Soc. Mass Spectrom. 14 1192 1203 10.1016/S1044-0305(03)00479-3 1:CAS:528:DC%2BD3sXnvFahu74%3D (Pubitemid 37204970)
56. Armentrout, P. B.; Heaton, A. L. Thermodynamics and Mechanisms of Protonated Diglycine Decomposition: A Computational Study. J. Am. Soc. Mass Spectrom.; in press (2011).