Mechanisms for the Proton Mobility-Dependent Gas-Phase Fragmentation Reactions of S-alkyl Cysteine Sulfoxide-Containing Peptide Ions

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 9, 2007, Pages 1690-1705

  Froelich, Jennifer M ^a   Reid, Gavin E ^a,b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; HYDROGEN PEROXIDE; MASS SPECTROMETRY; OXIDATION; PEPTIDES; PROTONATION;

ELIMINATION REACTION; GAS-PHASE FRAGMENTATION; PROTON MOBILITY; TANDEM MASS SPECTROMETRY;

REACTION KINETICS;

ALKYL GROUP; ALKYLATING AGENT; CARBON DIOXIDE; CYSTEINE DERIVATIVE; DEHYDROALANINE; ION; PEPTIDE; SULFENIC ACID DERIVATIVE; WATER;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; DATA BASE; DISSOCIATION; ELIMINATION REACTION; ENERGY TRANSFER; FRAGMENTATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION KINETICS; PHASE TRANSITION; PROTON TRANSPORT; TANDEM MASS SPECTROMETRY;

COMPUTER SIMULATION; CYSTEINE; DEUTERIUM EXCHANGE MEASUREMENT; IONS; MODELS, CHEMICAL; MODELS, MOLECULAR; PEPTIDES; PHASE TRANSITION; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFOXIDES;

BOVINAE;

EID: 34548130652     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2007.06.014     Document Type: Article

References (20)

1. Sechi S., and Chait B.T. Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification. Anal. Chem. 70 (1998) 5150-5158
2. Simpson R.J., Connelly L.M., Eddes J.S., Pereira J.J., Moritz R.L., and Reid G.E. Proteomic Analysis of the Human Colon Carcinoma Cell Line (LIM 1215): Development of a Membrane Protein Database. Electrophoresis 21 (2000) 1707-1732
3. Moritz R.L., Eddes J.S., Reid G.E., and Simpson R.J. S-Pyridylethylation of Intact Polyacrylamide Gels and in-Situ Digestion of Electrophoretically-separated Proteins: A Rapid Mass Spectrometric Method for Identifying Cysteine-Containing Peptides. Electrophoresis 17 (1996) 907-917
4. Shevchenko A., Wilm M., Vorm O., and Mann M. Mass Spectrometric Sequencing of Proteins from Silver-Stained Polyacrylamide Gels. Anal. Chem. 68 (1996) 850-858
5. Swiderek K.M., Davis M.T., and Lee T.D. The Identification of Peptide Modifications Derived from Gel-Separated Proteins Using Electrospray Triple Quadrupole and Ion Trap Analyses. Electrophoresis 19 (1998) 989-997
6. Steen H., and Mann M. Similarity Between Condensed Phase and Gas Phase Chemistry: Fragmentation of Peptides Containing Oxidized Cysteine Residues and its Implications for Proteomics. J. Am. Soc. Mass Spectrom. 12 (2001) 228-232
7. Yagüe J., Núñez A., Boix M., Esteller M., Alfonso P., and Casal J.I. Oxidation of Carboxyamidomethyl Cysteine may add Complexity to Protein Identification. Proteomics 5 (2005) 2761-2768
8. Chowdhury S.M., Munske G.R., Ronald R.C., and Bruce J.E. Evaluation of Low Energy CID and ECD Fragmentation Behavior of Mono-oxidized Thio-Ether Bonds in Peptides. J. Am. Soc. Mass Spectrom. 18 (2007) 493-501
9. Hunt D.F., Yates III J.R., Shabanowitz J., Winston S., and Hauer C.R. Protein Sequencing by Tandem Mass Spectrometry. Proc. Natl. Acad. Sci. U.S.A. 83 (1986) 6233-6237
10. Eng J.K., McCormack A.L., and Yates III J.R. An Approach to Correlate Tandem Mass Spectral Data of Peptides with Amino Acid Sequences in a Protein Database. J. Am. Soc. Mass Spectrom. 5 (1994) 976-989
11. Perkins D.N., Pappin D.J.C., Creasy D.M., and Cottrell J.S. Probability-Based Protein Identification by Searching Sequence Databases using Mass Spectrometry Data. Electrophoresis 20 (1999) 3551-3567
12. Gruhler A., Olsen J.V., Mohammed S., Mortensen P., Faergeman N.J., Mann M., and Jensen O.N. Quantitative Phosphoproteomics Applied to the Yeast Pheromone Signaling Pathway. Mol. Cell. Proteomics. 4 (2005) 310-327
13. 3. Rapid Commun. Mass Spectrom. 19 (2005) 3626-3632
14. Reid G.E., Roberts K.D., Kapp E.A., and Simpson R.J. Statistical and Mechanistic Approaches to Understanding the Gas-Phase Fragmentation Behavior of Methionine Sulfoxide-Containing Peptides. J. Prot. Res. 3 (2004) 751-759
15. Kapp E.A., Schütz F., Reid G.E., Eddes J.S., Moritz R.L., O'Hair R.A.J., Speed T.P., and Simpson R.J. Mining a Tandem Mass Spectrometry Database to Determine the Trends and Global Factors Influencing Peptide Fragmentation. Anal. Chem. 75 (2003) 6251-6264
16. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratman 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., and Pople J.A. Gaussian 98, Revision A.7 (1998), Gaussian, Inc, Pittsburgh, PA
17. Yang F., Stenoien D.L., Strittmatter E.F., Wang J., Ding L., Lipton M.S., Monroe M.E., Nicora C.D., Gristenko M.A., Tang K., Fang R., Adkins J.N., Camp D.G., Chen D.J., and Smith R.D. Phosphoproteome Profiling of Human Skin Fibroblast Cells in Response to Low- and High-Dose Irradiation. J. Prot. Res. 5 (2006) 1252-1260
18. Beausoleil S.A., Villén J., Gerber S.A., Rush J., and Gygi S.P. A Probability-Based Approach for High-Throughput Protein Phosphorylation Analysis and Site Localization. Nat. Biotechnol. 24 (2006) 1285-1292
19. Amungama M., Roberts K.D., and Reid G.E. Mechanisms for the Selective Gas-Phase Fragmentation Reactions of Methionine Side Chain Fixed Charge Sulfonium Ion-Containing Peptides. J. Am. Soc. Mass Spectrom. 17 (2006) 1631-1642
20. Hunter E.P., and Lias S.G. Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update. J. Phys. Chem. Ref. Data 27 (1998) 413-656