Can α- and β-Alanine Containing Peptides Be Distinguished Based on the CID Spectra of Their Protonated Ions?

Journal of the American Society for Mass Spectrometry

Volumn 19, Issue 12, 2008, Pages 1743-1754

  Lam, Adrian K Y ^a,b   Ramarathinam, Sri H ^a,b   Purcell, Anthony W ^a,b   O'Hair, Richard A J ^a,b,c  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c Australian Government Australian Research Council   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINES; CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; DIFFERENTIATION (CALCULUS); ELECTROLYSIS; EXPERIMENTS; NITROGEN COMPOUNDS; PEPTIDES; PORT TERMINALS; PROBABILITY DENSITY FUNCTION; PROTEINS; SULFUR COMPOUNDS;

ALANINE RESIDUES; CID SPECTRUMS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT CALCULATIONS; DI PEPTIDES; FRAGMENT IONS; FRAGMENTATION REACTIONS; INDUCED DISSOCIATIONS; PROTONATED; RELATIVE ABUNDANCES; STATE ENERGIES; TERMINAL RESIDUES;

IONS;

ALANINE; BETA ALANINE; PEPTIDE DERIVATIVE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; COLLISIONALLY ACTIVATED DISSOCIATION; FRAGMENTATION REACTION; ISOMERISM; PROTEIN STRUCTURE; PROTON TRANSPORT; THERMODYNAMICS;

ALANINE; BETA-ALANINE; DIPEPTIDES; MOLECULAR STRUCTURE; PROTONS; TANDEM MASS SPECTROMETRY; THERMODYNAMICS;

EID: 56949083494     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.09.007     Document Type: Article

References (55)

1. O'Hair R.A.J., and Reid G.E. Neighboring Group Versus cis-Elimination Mechanisms for Side Chain Loss from Protonated Methionine, Methionine Sulfoxide, and Their Peptides. Eur. J. Mass Spectrom 5 (1999) 325-334
2. Reid G.E., Simpson R.J., and O'Hair R.A.J. Leaving Group and Gas Phase Neighboring Group Effects in the Side Chain Losses from Protonated Serine and Its Derivatives. J. Am. Soc. Mass Spectrom 11 (2000) 1047-1060
3. Lioe H., O'Hair R.A.J., and Reid G.E. Gas-Phase Reactions of Protonated Tryptophan. J. Am. Soc. Mass Spectrom 15 (2004) 65-76
4. Lioe H., and O'Hair R.A.J. Neighboring Group Processes in the Deamination of Protonated Phenylalanine Derivatives. Org. Biomol. Chem 3 (2005) 3618-3628
5. Dookeran N.N., Yalcin T., and Harrison A.G. Fragmentation Reactions of Protonated α-amino acids. J. Mass Spectrom 31 (1996) 500-508
6. Harrison A.G., and ; Y.T. Proton Mobility in Protonated Amino Acids and Peptides. Int. J. Mass Spectrom. Ion Processes 165/166 (1997) 339-347
7. O'Hair R.A.J. The Role of Nucleophile-Electrophile Interactions in the Unimolecular and Bimolecular Gas-Phase Ion Chemistry of Peptides and Related Systems. J. Mass Spectrom 35 (2000) 1377-1381
8. Schlosser A., and Lehmann W.D. Five-Membered Ring Formation in Unimolecular Reactions of Peptides: A Key Structural Element Controlling Low-Energy Collision-Induced Dissociation of Peptides. J. Mass Spectrom 35 (2000) 1382-1390
9. Polce M.J., Ren D., and Wesdemiotis C. Dissociation of the Peptide Bond in Protonated Peptides. J. Mass Spectrom 35 (2000) 1391-1398
10. Wysocki V.H., Tsaprailis 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
11. Paizs B., and Suhai S. Fragmentation Pathways of Protonated Peptides. Mass Spectrom. Rev 24 (2005) 508-548
12. Barlow C.K., and O'Hair R.A.J. Gas Phase Peptide Fragmentation: From Understanding the Fundamentals to the Design of New Proteomics Tools. J. Mass Spectrom (2008) in press (DOI:10.1002/jms. 1469)
13. Aguilar M.I., Purcell A.W., Devi R., Lew R., Rossjohn J., Smith A.I., and Perlmutter P. β-Amino Acid-Containing Hybrid Peptides-New Opportunities in Peptidomimetics. Org. Biomol. Chem 5 (2007) 2884-2890
14. Daniels D.S., Petersson E.J., Qiu J.X., and Schepartz A. High-Resolution Structure of a β-Peptide Bundle. J. Am. Chem. Soc 129 (2007) 1532-1533
15. Wu J., Gard E., Bregar J., Green M.K., and Lebrilla C.B. Studies of Nearest-Neighbor Interactions Between Amino Acids in Gas-Phase Protonated Peptides. J. Am. Chem. Soc 117 (1995) 9900-9905
16. Hahn I., and Wesdemiotis C. Protonation Thermochemistry of β-Alanine. An Evaluation of Proton Affinities and Entropies Determined by the Extended Kinetic Method. Int. J. Mass Spectrom 222 (2003) 465-479
17. Abirami S., Xing Y.M., Tsang C.W., and Ma N.L. Theoretical Study of α/β Alanine and Their Protonated/Alkali Metal Cationized Complexes. J. Phys. Chem. A 109 (2005) 500-506
18. Tsang C.W., and Harrison A.G. Chemical Ionization of Amino Acids. J. Am. Chem. Soc 98 (1976) 1301-1308
19. Wysocki V.H., Burinsky D.J., and Cooks R.G. Competitive Dehydration and Deamination of α,ω-Amino Alcohols and α,ω-Amino Acids in the Gas Phase. J. Org. Chem 50 (1985) 1287-1291
20. Parker C.D., and Hercules D.M. Laser Mass Spectra of Simple Aliphatic and Aromatic Amino Acids. Anal. Chem 57 (1985) 698-704
21. Rosnack K.J., Somayajula K.V., Sharkey A.G., Jensen N.J., and Hercules D.M. Determination of Water Loss Mechanism in Amine Terminus Amino Acids Using Laser Mass Spectrometry. Appl. Spectrosc 43 (1989) 1087-1092
22. Cheng M.-K.J., Chan O.-Y.O., Abirami S., Ma N.L., and Tsang C.W. A Theoretical Study on Fragmentation Pathways and Mechanisms of Protonated β-Alanine. Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, March (2005)
23. Chan O.-Y.O., Cheng M.-K.J., Ma N.L., and Tsang C.W. Mass Spectrometric Fragmentation of Protonated Peptides Containing β-Amino Acids (2005) Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, March
24. Talaty E.R., Cooper T.J., Osburn S., and Van Stipdonk M.J. Collision-Induced Dissociation of Protonated Tetrapeptides Containing β-alanine, γ-aminobutyric acid, ε-aminocaproic acid, or 4-aminomethylbenzoic acid residues. Rapid Commun. Mass Spectrom 20 (2006) 3443-3455
25. Reddy P., Nagi, Srikanth R., Swamy N.S., Srinivas R., Sharma G.V.M., Nagendar P., and Krishna P.R. Differentiation of Boc-α,β- and β,α-Peptides and a Pair of Diastereomeric β,α-Dipeptides by Positive and Negative Ion Electrospray Tandem Mass Spectrometry (ESI-MS/MS). J. Mass Spectrom 40 (2005) 1429-1438
26. Schreiber J.V., Quadroni M., and Seebach D. Sequencing of β-Peptides by Mass Spectrometry. Chimia 53 (1999) 621-626
27. Roepstorff P., and Fohlman J. Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides. J. Biol. Mass Spectrom 11 (1994) 601
28. Biemann K., and Papayannopoulos I.A. Amino Acid Sequencing of Proteins. Acc. Chem. Res 27 (1994) 370-378
29. Wee S., O'Hair R.A.J., and McFadyen W.D. Side Chain Radical Losses from Radical Cations Allows Distinction of Leucine and Isoleucine Residues in the Isomeric Peptides Gly-XXX-Arg. Rapid Commun. Mass Spectrom 16 (2002) 884-890
30. Vaisar T., Gatlin C.L., Rao R.D., Seymour J.L., and Tureček F. 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 36 (2001) 306-316
31. Feenstra R.W., Stokkingreef E.H.M., Reichwein A.M., Lousberg W.B.H., and Ottenheijm H.C.J. Oxidative Preparation of Optically Active N-Hydroxy-α-Amino Acid Amides. Tetrahedron 46 (1990) 1745-1756
32. Montalbetti C.A.G.N., and Falque V. Amide Bond Formation and Peptide Coupling. Tetrahedron 61 (2005) 10827-10852
33. 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 Rev. B 04 (2003), Gaussian, Inc, Pittsburgh, PA
34. Scott A.P., and Radom L. Harmonic Vibrational Frequencies: An Evaluation of Hartree-Fock, Moeller-Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors. J. Phys. Chem 100 (1996) 16502-16513
35. + ions. J. Am. Soc. Mass Spectrom 9 (1998) 945-956
36. Arend M., Westermann B., and Risch N. Modern Variants of the Mannich Reaction. Angewandte Chemie Int. Ed 37 (1998) 1045-1070
37. Reid G.E., Simpson R.J., and O'Hair R.A.J. Probing the Fragmentation Reactions of Protonated Glycine Oligomers via Multistage Mass Spectrometry and Gas Phase H/D Exchange in a Modified Ion Trap. Int. J. Mass Spectrom 190/191 (1999) 209-230
38. Pingitore F., Polce M.J., Wang P., Wesdemiotis C., and Paizs B. Intramolecular Condensation Reactions in Protonated Dipeptides: Carbon Monoxide, Water, and Ammonia Losses in Competition. J. Am. Soc. Mass Spectrom 15 (2004) 1025-1038
39. Bythell B.J., Barofsky D.F., Pingitore F., Polce M.J., Wang P., Wesdemiotis C., and Paizs B. 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 18 (2007) 1291-1303
40. 1 Ions Derived from Aliphatic Amino Acids: A Combined Experimental and Ab Initio Study. Rapid Commun. Mass Spectrom 14 (2000) 1220-1225
41. + Peptide Fragments Reveals the Presence of the Acylium Ion Structure. Rapid Commun. Mass Spectrom 14 (2000) 2242-2246
42. Polfer N.C., Oomens J., Suhai S., and Paizs B. 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 (2007) 5887-5897
43. Polfer N.C., Bohrer B.C., Plasencia M.D., Paizs B., and Clemmer D.E. On the Dynamics of Fragment Isomerization in Collision-Induced Dissociation of Peptides. J. Phys. Chem. A 112 (2008) 1286-1293
44. Riba-Garcia I., Giles K., Bateman R.H., and Gaskell S.J. Evidence for Structural Variants of a- and b-Type Peptide Fragment Ions Using Combined Ion Mobility/Mass Spectrometry. J. Am. Soc. Mass Spectrom 19 (2008) 609-613
45. Morgan D.G., and Bursey M.M. Tandem Mass Spectral Decompositions of Protonated N-Acyloligoalanines and N-Acyloligoglycines as Models for Those of the Protonated Free Oligopeptides. Biol. Mass Spectrom 22 (1993) 502-510
46. Morgan D.G., and Bursey M.M. A Linear Free-Energy Correlation in the Low-Energy Tandem Mass Spectra of Protonated Tripeptides Gly-Gly-Xxx. Org. Mass Spectrom 29 (1994) 354-359
47. Morgan D.G., and Bursey M.M. Linear Energy Correlation in the Low-Energy Tandem Mass Spectra of Protonated Tripeptides Xxx-Gly-Gly but failure for Gly-Xxx-Gly. J. Mass Spectrom 30 (1995) 290-295
48. Klassen J.S., and Kebarle P. Collision-Induced Dissociation Threshold Energies of Protonated Glycine, Glycinamide, and Some Related Small Peptides and Peptide Amino Amides. J. Am. Soc. Mass Spectrom 119 (1997) 6552-6563
49. Eckart K., Holthausen M.C., Koch W., and Spiess J. Mass Spectrometric and Quantum Mechanical Analysis of Gas-Phase Formation, Structure, and Decomposition of Various b2 Ions and Their Specifically Deuterated Analogs. J. Am. Soc. Mass Spectrom 9 (1998) 1002-1011
50. Harrison A.G., Csizmadia I.G., and Tang T.-H. Structure and Fragmentation of b2 ions in Peptide Mass Spectra. J. Am. Soc. Mass Spectrom 11 (2000) 427-436
51. Balta B., Aviyente V., and Lifshitz C. Elimination of water from the carboxyl group of GlyGlyH+. J. Am. Soc. Mass Spectrom 14 (2003) 1192-1203
52. Paizs B., Schnoelzer M., Warnken U., Suhai S., and Harrison A.G. Cleavage of the Amide Bond of Protonated Dipeptides. Phys. Chem., Chem. Phys 6 (2004) 2691-2699
53. Yao C., Syrstad E.A., and Tureček F. Electron Transfer to Protonated β-Alanine N-Methylamide in the Gas Phase: An Experimental and Computational Study of Dissociation Energetics and Mechanisms. J. Phys. Chem. A 111 (2007) 4167-4180
54. Tintaru A., Benchabane Y., Boyer B., Humbel S., and Charles L. Differentiation of Heterocyclic Regioisomers: A Combined Tandem Mass Spectrometry and Computational Study of N-Acridin-4-Ylbenzylamide and N-Acridin-2-yl-Benzylamide. Rapid Commun. Mass Spectrom 22 (2008) 687-693
55. Hohmann L.J., Eng J.K., Gemmill A., Klimek J., Vitek O., Reid G.E., and Martin D.B. Quantification of the Compositional Information Provided by Immonium Ions on a Quadrupole-Time-of-Flight Mass Spectrometer. Anal. Chem 80 (2008) 5596-5606