Near-UV Photodissociation of Tryptic Peptide Cation Radicals. Scope and Effects of Amino Acid Residues and Radical Sites

Overview

Journal J Am Soc Mass Spectrom

Specialty Chemistry

Date 2017 Feb 4

PMID 28155086

Citations 3

Authors

Huong T H Nguyen

Frantisek Turecek

Affiliations

Soon will be listed here.

Abstract

Peptide cation-radical fragment ions of the z-type, [AXAR], [AXAK], and [XAR], where X = A, C, D, E, F, G, H, K, L, M, N, P, Y, and W, were generated by electron transfer dissociation of peptide dications and investigated by MS-near-ultraviolet photodissociation (UVPD) at 355 nm. Laser-pulse dependence measurements indicated that the ion populations were homogeneous for most X residues except phenylalanine. UVPD resulted in dissociations of backbone CO─NH bonds that were accompanied by hydrogen atom transfer, producing fragment ions of the [y] type. Compared with collision-induced dissociation, UVPD yielded less side-chain dissociations even for residues that are sensitive to radical-induced side-chain bond cleavages. The backbone dissociations are triggered by transitions to second (B) excited electronic states in the peptide ion R-CH-CONH- chromophores that are resonant with the 355-nm photon energy. Electron promotion increases the polarity of the B excited states, R-CH-C(O)NH-, and steers the reaction to proceed by transfer of protons from proximate acidic C and amide nitrogen positions. Graphical Abstract ᅟ.

Citing Articles

w-Type ions formed by electron transfer dissociation of Cys-containing peptides investigated by infrared ion spectroscopy.

Kempkes L, Martens J, Berden G, Oomens J J Mass Spectrom. 2018; 53(12):1207-1213.

PMID: 30281881 PMC: 6283004. DOI: 10.1002/jms.4298.

Spontaneous Isomerization of Peptide Cation Radicals Following Electron Transfer Dissociation Revealed by UV-Vis Photodissociation Action Spectroscopy.

Imaoka N, Houferak C, Murphy M, Nguyen H, Dang A, Turecek F J Am Soc Mass Spectrom. 2018; 29(9):1768-1780.

PMID: 29340957 DOI: 10.1007/s13361-017-1871-0.

The Role of Electron Transfer Dissociation in Modern Proteomics.

Riley N, Coon J Anal Chem. 2017; 90(1):40-64.

PMID: 29172454 PMC: 5750139. DOI: 10.1021/acs.analchem.7b04810.

References

Brodbelt J . Photodissociation mass spectrometry: new tools for characterization of biological molecules. Chem Soc Rev. 2014; 43(8):2757-83. PMC: 3966968. DOI: 10.1039/c3cs60444f. View

Chung T, Hui R, Ledvina A, Coon J, Turecek F . Cascade dissociations of peptide cation-radicals. Part 1. Scope and effects of amino acid residues in penta-, nona-, and decapeptides. J Am Soc Mass Spectrom. 2012; 23(8):1336-50. PMC: 3619428. DOI: 10.1007/s13361-012-0408-9. View

Holm A, Hvelplund P, Kadhane U, Larsen M, Liu B, Nielsen S . On the mechanism of electron-capture-induced dissociation of peptide dications from 15n-labeling and crown-ether complexation. J Phys Chem A. 2007; 111(39):9641-3. DOI: 10.1021/jp075943y. View

Chung T, Turecek F . Backbone and side-chain specific dissociations of z ions from non-tryptic peptides. J Am Soc Mass Spectrom. 2010; 21(8):1279-95. DOI: 10.1016/j.jasms.2010.02.018. View

Polfer N . Infrared multiple photon dissociation spectroscopy of trapped ions. Chem Soc Rev. 2011; 40(5):2211-21. DOI: 10.1039/c0cs00171f. View

Vaisar T, Gatlin C, Rao R, Seymour J, Turecek 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. 2001; 36(3):306-16. DOI: 10.1002/jms.135. View

Warren J, Tronic T, Mayer J . Thermochemistry of proton-coupled electron transfer reagents and its implications. Chem Rev. 2010; 110(12):6961-7001. PMC: 3006073. DOI: 10.1021/cr100085k. View

Pepin R, Turecek F . Kinetic ion thermometers for electron transfer dissociation. J Phys Chem B. 2015; 119(7):2818-26. DOI: 10.1021/jp510244d. View

Shaffer C, Martens J, Marek A, Oomens J, Turecek F . Photoleucine Survives Backbone Cleavage by Electron Transfer Dissociation. A Near-UV Photodissociation and Infrared Multiphoton Dissociation Action Spectroscopy Study. J Am Soc Mass Spectrom. 2016; 27(7):1176-85. DOI: 10.1007/s13361-016-1390-4. View

10.

Brodbelt J, Wilson J . Infrared multiphoton dissociation in quadrupole ion traps. Mass Spectrom Rev. 2009; 28(3):390-424. DOI: 10.1002/mas.20216. View

11.

Eva Fung Y, Chan T . Experimental and theoretical investigations of the loss of amino acid side chains in electron capture dissociation of model peptides. J Am Soc Mass Spectrom. 2005; 16(9):1523-35. DOI: 10.1016/j.jasms.2005.05.001. View

12.

Osburn S, Berden G, Oomens J, OHair R, Ryzhov V . Structure and reactivity of the N-acetyl-cysteine radical cation and anion: does radical migration occur?. J Am Soc Mass Spectrom. 2011; 22(10):1794-803. DOI: 10.1007/s13361-011-0198-5. View

13.

Viglino E, Lai C, Mu X, Chu I, Turecek F . Ground and Excited-Electronic-State Dissociations of Hydrogen-Rich and Hydrogen-Deficient Tyrosine Peptide Cation Radicals. J Am Soc Mass Spectrom. 2016; 27(9):1454-67. DOI: 10.1007/s13361-016-1425-x. View

14.

Biemann K . Appendix 5. Nomenclature for peptide fragment ions (positive ions). Methods Enzymol. 1990; 193:886-7. DOI: 10.1016/0076-6879(90)93460-3. View

15.

Reilly J . Ultraviolet photofragmentation of biomolecular ions. Mass Spectrom Rev. 2009; 28(3):425-47. PMC: 5056644. DOI: 10.1002/mas.20214. View

16.

Mayer J . Proton-coupled electron transfer: a reaction chemist's view. Annu Rev Phys Chem. 2004; 55:363-90. DOI: 10.1146/annurev.physchem.55.091602.094446. View

17.

Cox K, Gaskell S, Morris M, Whiting A . Role of the site of protonation in the low-energy decompositions of gas-phase peptide ions. J Am Soc Mass Spectrom. 2013; 7(6):522-31. DOI: 10.1016/1044-0305(96)00019-0. View

18.

Syka J, Coon J, Schroeder M, Shabanowitz J, Hunt D . Peptide and protein sequence analysis by electron transfer dissociation mass spectrometry. Proc Natl Acad Sci U S A. 2004; 101(26):9528-33. PMC: 470779. DOI: 10.1073/pnas.0402700101. View

19.

Lesslie M, Osburn S, van Stipdonk M, Ryzhov V . Gas-phase tyrosine-to-cysteine radical migration in model systems. Eur J Mass Spectrom (Chichester). 2015; 21(3):589-97. DOI: 10.1255/ejms.1341. View

20.

Hendricks N, Lareau N, Stow S, McLean J, Julian R . Bond-specific dissociation following excitation energy transfer for distance constraint determination in the gas phase. J Am Chem Soc. 2014; 136(38):13363-70. PMC: 4183596. DOI: 10.1021/ja507215q. View