Elimination of water from the carboxyl group of GlyGlyH+

Journal of the American Society for Mass Spectrometry

Volumn 14, Issue 10, 2003, Pages 1192-1203

  Balta, Bülent ^a   Aviyente, Viktorya ^a   Lifshitz, Chava ^b  

^a BOGAZICI UNIVERSITY   (Turkey)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

POLYPEPTIDES; PROBABILITY DENSITY FUNCTION; PROTONS; WATER;

CARBOXYL GROUPS;

CARBOXYLATION;

AMIDE; CARBON; CARBOXYL GROUP; DIGLYCINE; HYDROGEN; ION; NITROGEN; OXAZOLONE; OXYGEN; PEPTIDE; PIPERAZINEDIONE; WATER;

MASS SPECTROMETRY;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; ENERGY TRANSFER; ENTROPY; FRAGMENTATION REACTION; GEOMETRY; KINETICS; MASS SPECTROMETRY; MOLECULAR MODEL; PROTON TRANSPORT;

EID: 0141672282     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1044-0305(03)00479-3     Document Type: Article

References (34)

1. Biemann K., Martin S.A. Mass Spectrometric Determination of the Amino Acid Sequence of Peptides and Proteins. Mass Spectrom. Rev. 6:1987;1-76.
2. Biemann K. Sequencing of Peptides by Tandem Mass Spectrometry and High-Energy Collision Induced Dissociation. McCloskey J.A. Mass Spectrometry, Methods in Enzymology. 193:1990;455-479 Academic Press, San Diego.
3. Biemann K. Primary Studies of Peptides and Proteins. Matsuo T., Caprioli R.M., Gross M.L., Seyama Y. Biological Mass Spectrometry Present and Future . 1993;275-297 Wiley, New York.
4. Papayannopoulos I.A. The Interpretation of Collision-Induced Dissociation Tandem Mass Spectra of Peptides. Mass Spectrom. Rev. 14:1995;49-73.
5. Roepstorff P., Fohlman J. Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides. Biomed. Mass Spectrom. 11:1984;601.
6. Tsang C.W., Harrison A.G. Chemical Ionization of Amino Acids. J. Am. Chem. Soc. 98:1976;1301-1308.
7. Harrison A.G., Yalcin T. Proton Mobility in Protonated Amino Acids and Peptides. Int. J. Mass Spectrom. Ion Processes. 165/166:1997;339-347.
8. Paizs B., Csonka I.P., Lendvay G., Suhai S. Proton Mobility in Protonated Glycylglycine and N-Formylglycylglycinamide A Combined Quantum Chemical and RRKM Study . Rapid Commun. Mass Spectrom. 15:2001;637-650.
9. Dongré A.R., Jones J.L., Somogyi A., Wysocki V.H. Influence of Peptide Composition , Gas-Phase Basicity, and Chemical Modification on Fragmentation Efficiency Evidence for the Mobile Proton Model . J. Am. Chem. Soc. 118:1996;8365-8374.
10. Somogyi A., Wysocki V.H., Mayer I. The Effect of Protonation Site on Bond Strengths in Simple Peptides Application of ab initio and Modified Neglect of Differential Overlap Bond Order and Modified Neglect of Differential Overlap Energy Partitioning . J. Am. Soc. Mass Spectrom. 5:1994;704-717.
11. Mueller D.R., Eckersley M., Richter W. Hydrogen Transfer Reactions in the Formation of "y + 2" Sequence Ions from Protonated Peptides. Org. Mass Spectrom. 23:1988;217-222.
12. Cordero M.M., Houser J.J.Wesdemiotis C.The Neutral Products Formed During Backbone Fragmentation of Protonated Peptides in Tandem Mass Spectrometry. Anal. Chem. 65:1993;1594-1601.
13. Yalcin T., Khouw C., Csizmadia I.G., Peterson M.R., Harrison A.G. Why are B Ions Stable Species in Peptide Spectra? J. Am. Soc. Mass Spectrom. 6:1995;1165-1174.
14. n (n ≥ 3) Ions in Peptide Spectra. J. Am. Soc. Mass Spectrom. 7:1996;233-242.
15. Nold M.J., Wesdemiotis C., Yalcin T., Harrison A.G. Amide Bond Dissociation in Protonated Peptides. Structures of the N-Terminal Ionic and Neutral Fragments. Int. J. Mass Spectrom. Ion Processes. 164:1997;137-153.
16. 2 Ions in Peptide Mass Spectra. J. Am. Soc. Mass Spectrom. 11:2000;427-436.
17. Arnot D., Kottmeier D., Yates N., Shabanowitz J., Hunt D.F. Fragmentation of Multiply Protonated Peptides Under Low Energy Conditions. 1994;Proceedings of the 42nd ASMS Conference on Mass Spectrometry and Allied Topics, Chicago, IL. p. 470 June, 1994.
18. + Ions of Protonated Peptides. An ab initio Study. Rapid Commun. Mass Spectrom. 14:2000;746-755.
19. + Ions. J. Am. Soc. Mass Spectrom. 9:1998;945-956.
20. Rodriquez C.F., Cunje A., Shoeib T., Chu I.K., Hopkinson A.C., Siu K.W.M. Proton Migration and Tautomerism in Protonated Triglycine. J. Am. Chem. Soc. 123:2001;3006-3012.
21. 2 Ions and Their Specifically Deuterated Analogs. J. Am. Soc. Mass Spectrom. 1998, 9, 1002-1001.
22. Klassen J.S., Kebarle P. Collision-Induced Dissociation Threshold Energies of Protonated Glycine, Glycinamide, and Some Related Small Peptides and Peptide Amino Amides. J. Am. Chem. Soc. 119:1997;6552-6563.
23. Reid E.G., Simpson R.J., O'Hair R.A.J. Probing the Fragmentation Reactions of Protonated Glycine Oligomers via Multistage Mass Spectrometry and Gas Phase Ion Molecule Hydrogen/Deuterium Exchange. Int. J. Mass Spectrom. 190/191:1991;209-230.
24. + and CO. Rapid Commun Mass Spectrom. 10:1996;1237-1239.
25. Zhang K., Zimmerman D.M., Chung-Phillips A., Cassady C.J. Exprimental and ab initio Studies of the Gas-Phase Basicities of Polyglycines. J. Am. Chem. Soc. 115:1993;10812-10822.
26. Paizs B., Suhai S. Theoretical Study of the Main Fragmentation Pathways for Protonated Glycylglycine. Rapid Commun. Mass Spectrom. 15:2001;651-663.
27. Becke A.D. Density Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 98:1993;5648-5652.
28. Lee C., Yang W., Parr R.G. Development of Colle-Salvetti Correlation Energy Formula into a Functional of the Electron Density. Phys. Rev. B. 37:1988;785-789.
29. Balta B., Basma M., Aviyente V., Zhu C., Lifshitz C. Structures and Reactivity of Gaseous Glycine and its Derivatives. Int. J. Mass Spectrom. 201:2000;69-85.
30. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A.J.r.;, Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., Pople J.A. Gaussian 98, Revision A7. 1998;Gaussian, Inc, Pittsburgh, PA.
31. Foster J.P., Weinhold F. Natural Hybrid Orbitals. J. Am. Chem. Soc. 102:1980;7211-7218.
32. Glendening, E. D. Reed, A. E. Carpenter, J. E. Weinhold, F. NBO Program, Version 3.1.
33. Paizs B., Suhai S. Combined Quantum Chemical and RRKM Modeling of the Main Fragmentation Pathways of Protonated GGG. I. Cis-trans Isomerization Around Protonated Amide Bonds. Rapid Commun. Mass Spectrom. 15:2001;2307-2323.
34. Uggerud E. The Unimolecular Chemistry of Protonated Glycine and the Proton Affinity of Glycine A Computational Model. Theor. Chem. Acc. 97:1997;313-316.