Non-zwitterionic structures of aliphatic-only peptides mediated the formation and dissociation of gas phase radical cations

Journal of Mass Spectrometry

Volumn 41, Issue 7, 2006, Pages 931-938

  Lam, Corey N W ^a   Ruan, Eric D L ^a   Ma, C Y ^a   Chu, Ivan K ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Copper(II) complexes; Electron transfer; Non zwitterionic structures; Peptide fragmentation; Radical cationic peptides

Indexed keywords

COMPLEXATION; DISSOCIATION; ELECTRON TRANSPORT PROPERTIES; MASS SPECTROMETRY; MICROSTRUCTURE; POSITIVE IONS;

COPPER(II) COMPLEXES; NON-ZWITTERIONIC STRUCTURES; PEPTIDE FRAGMENTATION; RADICAL CATIONIC PEPTIDES;

AMINO ACIDS;

AMPHOLYTE; CARBON; CARBOXYLIC ACID; CATION; CHOLESTEROL MONOOXYGENASE (SIDE CHAIN CLEAVING); GLYCINE; ISOLEUCINE; LEUCINE; METAL COMPLEX; PEPTIDE DERIVATIVE; RADICAL; TRIPEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; ELECTRON TRANSPORT; FEASIBILITY STUDY; GAS; PRIORITY JOURNAL; PROTEIN DEGRADATION; SYNTHESIS;

ACETYLATION; CATIONS; CIRCULAR DICHROISM; COPPER; GASES; METHYLATION; PEPTIDES;

EID: 33746293271     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1052     Document Type: Article

References (41)

1. Biemann K. Mess Spectrometry Organic Chemical Applications. McGraw-Hill: New York, 1962.
2. 2. J. Am. Chem. Soc. 1962; 84: 3192.
3. Kemp M, Roiterg A, Mujica V, Wanta T, Ratner MA. Molecular wires: extended coupling and disorder effects. J. Phys. Chem. 1996; 100: 8349.
4. Schlag EW, Lin SH, Weinkauf R, Rentzepis PM. Dynamical principles in biological processes. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 1358.
5. Levis RJ. Laser desorption and ejection of biomolecules from the condensed phase into the gas phase. Annu. Rev. Phys. Chem. 1994; 45: 483.
6. Chu IK, Rodriquez CF, Lau TC, Hopkinson AC, Siu KWM. Molecular radical cations of oligopeptides. J. Phys. Chem. B 2000; 104: 3393.
7. Chu IK, Rodriquez CF, Lau TC, Hopkinson AC, Siu KWM. Formation of molecular radical cations of enkephalin derivatives via collision-induced dissociation of electrospray-generated Copper (II) complex ions of amines and peptides. J. Am. Soc. Mass Spectrom. 2001; 12: 1114.
8. Bagheri-Majdi E, Ke Y, Orlova G, Hopkinson AC, Siu KWM. Copper-mediated peptide radical ions in the gas phase. J. Phys. Chem. B 2004; 108: 11170.
9. Wee S, O'Hair RAJ, McFadyen WD. 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. 2002; 16: 884.
10. Wee S, O'Hair RAJ, McFadyen WD. Comparing the gas-phase fragmentation reactions of protonated and radical cations of the tripeptides GXR. Int. J. Mass Spectrom. 2004; 234: 101.
11. Barlow CK, Wee S, McFadyen WD, O'Hair RAJ. Designing copper(II) ternary complexes to generate radical cations of peptides in the gas phase: role of the auxiliary ligand. Dalton Trans. 2004; 3199.
12. Barlow CK, McFadyen WD, O'Hair RAJ. Formation of cationic peptide radicals by gas-phase redox reactions with trivalent chromium, manganese, iron, and cobalt complexes. J. Am. Chem. Soc. 2005; 127: 6109.
13. II(12-crown-4). Rapid Commun. Mass Spectrom. 2004; 18: 1798.
14. II tripeptide complexes containing sterically encumbered terpyridine ligands. J. Am. Soc. Mass Spectrom. 2005; 16: 763.
15. 2+ do exist. Chem. Phys. Lett. 2001; 343: 258.
16. Gatlin CL, Turecek F, Vaisar T. Copper(II) amino acid complexes in the gas phase. J. Am. Chem. Soc. 1995; 117: 3637.
17. Seymour JL, Turecek F. Structure, energetics and reactivity of ternary complexes of amino acids with Cu(II) and 2,2-bipyridine by density functional theory. A combination of radical-induced and spin-remote fragmentations. J. Mass Spectrom. 2002; 37: 533.
18. 3+. J. Am. Soc. Mass Spectrom. 2005; 16: 1795.
19. Gatlin CL, Rao RD, Turecek F, Vaisar T. Carboxylate and amine terminus directed fragmentations in gaseous dipeptide complexes with copper(II) and diimine ligands formed by electrospray. Anal. Chem. 1996; 68: 263.
20. Vaisar T, Gatlin CL, Rao RD, Seymour JL, 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. Mess Spectrom. 2001; 36: 306.
21. Lam CNW, Siu SO, Orlova G, Chu IK. Macrocyclic effect of auxiliary ligand on the gas-phase dissociation of ternary copper(II)-GGX complexes. Rapid Commun. Mass Spectrom. 2006; 20: 790.
22. Gray HB, Malmstrom BG, Williams RJP. Copper coordination in blue proteins. J. Biol. Inorg. Chem. 2000; 5: 551.
23. Williams RJP. Energized (entatic) states of groups and of secondary structures in proteins and metalloproteins. Eur. J. Biochem. 1995; 234: 363.
24. Vallee BL, Williams RJP. Metalloenzymes: the entatic nature of their active sites. Proc. Natl. Acad. Sci. U.S.A. 1968; 59: 498.
25. Hodyss R, Cox HA, Beauchamp JL. Bioconjugates for tunable peptide fragmentation: free radical initiated peptide sequencing (FRIPS). J. Am. Chem. Soc. 2005; 127: 12436.
26. Chan WC, White PD. Fmoc Solid Phase Peptide Synthesis: A Practical Approach. Oxford: New York, 2000.
27. 2. Inorg. Chem. 1983; 22: 2858.
28. 2+-glycine. J. Phys. Chem. B 1999; 103: 2310.
29. 2+(M = Be, Mg, Ca, Sr, Ba), in the gas phase: Intrinsic effect of cation size on zwitterion stability. J. Phys. Chem. A 2000; 104: 9793.
30. Wyttenbach T, Witt M, Bowers MT. On the stability of amino acid zwitterions in the gas phase: the influence of derivatization, proton affinity, and alkali ion addition. J. Am. Chem. Soc. 2000; 122: 3458.
31. 2+): Existence of zwitterionic structures? Chem. - Eur. J. 2000; 6: 4393.
32. Jensen JH, Gordon MS. The conformational potential energy surface of glycine: a theoretical study. J. Am. Chem. Soc. 1991; 113: 7917.
33. Iijima K, Tanaka K, Onuma S. Main conformer of gaseous glycine - molecular-structure and rotational barrier from electron-diffraction data and rotational-constants. J. Mol. Struct. 1991; 246: 257.
34. Stepanian SG, Reva ID, Radchenko ED, Rosado MTS, Duarte MLTS, Fausto R, Adamowicz L. Matrix-isolation infrared and theoretical studies of the glycine conformers. J. Phys. Chem. A 1998; 102: 1041.
35. Stepanian SG, Reva ID, Radchenko ED, Adamowicz L. Conformational behavior of α-talanine. Matrix-isolation infrared and theoretical DFT and ab initio study. J. Phys. Chem. A 1998; 102: 4623.
36. Stepanian SG, Reva ID, Radchenko ED, Adamowicz L. Combined matrix-isolation infrared and theoretical DFT and ab initio study of the nonionized valine conformers. J. Phys. Chem. A 1999; 103: 4404.
37. Blanco S, Lesarri A, Lopez JC, Alonso JL. The gas-phase structure of alanine. J. Am. Chem. Soc. 2004; 126: 11675.
38. Lesarri A, Cocinero EJ, Lopez JC, Alonso JL. The shape of neutral valine. Angew. Chem., Int. Ed. Engl. 2004; 43: 605.
39. Jensen JH, Gordon MS. On the number of water molecules necessary to stabilize the glycine zwitterion. J. Am. Chem. Soc. 1995; 117: 8159.
40. Ding YB, Krogh-Jespersen K. The 1:1 glycine zwitterion-water complex: an ab initio electronic structure study. J. Comput. Chem. 1996; 17: 338.
41. Hopkinson AC, Siu KWM. Peptide radical cations. In Basic Aspects and Principles of Mass Spectrometry Applied to Biomolecules, Wiley InterScience, (in press).