Structural characterization by infrared multiple photon dissociation spectroscopy of protonated gas-phase ions obtained by electrospray ionization of cysteine and dopamine

Analytical and Bioanalytical Chemistry

Volumn 399, Issue 7, 2011, Pages 2463-2473

  Steill, Jeffrey D ^a,d   Szczepanski, Jan ^b   Oomens, Jos ^a,c   Eyler, John R ^b   Brajter Toth, Anna ^b  

^a FOM INSTITUTE FOR PLASMA PHYSICS RIJNHUIZEN   (Netherlands)

^b University of Florida   (United States)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

^d Sandia/California   (United States)

Author keywords

Bioanalytical methods; Cysteine; Dimers; Dopamine; Laser spectroscopy; Mass spectrometry

Indexed keywords

AMINE GROUPS; BIOANALYTICAL METHODS; COVALENTLY BOUND; CYSTEINE; DFT CALCULATION; DISULFIDE BONDS; DISULFIDE LINKAGES; DOPAMINE; ELECTROSPRAYS; ETHYLAMINE; GAS PHASE IONS; GASPHASE; INFRARED MULTIPLE PHOTON DISSOCIATIONS; INTRAMOLECULAR HYDROGEN BONDING; IR ABSORPTION SPECTRA; IR BANDS; MAJOR IONS; MASS SPECTRA; PROTONATED; REDOX PROPERTY; SIDE CHAINS; STRUCTURAL CHARACTERIZATION;

ABSORPTION; ABSORPTION SPECTROSCOPY; AMINO ACIDS; BRAIN; CONFORMATIONS; DISSOCIATION; ELECTROSPRAY IONIZATION; FREE ELECTRON LASERS; HYDROGEN BONDS; INFRARED ABSORPTION; INFRARED LASERS; IONIZATION OF GASES; IONS; LASER SPECTROSCOPY; LASER THEORY; LASERS; LIGHT ABSORPTION; MASS SPECTROMETERS; MASS SPECTROMETRY; MEDICAL NANOTECHNOLOGY; MONOMERS; PHOTOIONIZATION; PHOTONS; PROTONATION; PROTONS;

DIMERS;

CYSTEINE; DOPAMINE; ION; PROTON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DIMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; GAS; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; PHOTON; THERMODYNAMICS;

CYSTEINE; DIMERIZATION; DOPAMINE; GASES; HYDROGEN BONDING; IONS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTONS; PROTONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; THERMODYNAMICS;

EID: 79951811226     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-010-4582-y     Document Type: Article

References (54)

1. JA Starkey Y Mechref J Muzikar WJ McBride MV Novotny 2006 Determination of salsolinol and related catecholamines through on-line preconcentration and liquid chromatography/atmospheric pressure photoionization mass spectrometry Anal Chem 78 10 3342 3347 1:CAS:528:DC%2BD28Xjt1KmtLg%3D 10.1021/ac051863j
2. JE Chipuk MH Gelb JS Brodbelt 2010 Rapid and selective screening for sulfhydryl analytes in plasma and urine using surface-enhanced transmission mode desorption electrospray ionization mass spectrometry Anal Chem 82 10 4130 4139 10.1021/Ac100242b 1:CAS:528:DC%2BC3cXkvV2rs7k%3D 10.1021/ac100242b
3. R Aebersold M Mann 2003 Mass spectrometry-based proteomics Nature 422 6928 198 207 1:CAS:528:DC%2BD3sXhvFKgs7s%3D 10.1038/nature01511 (Pubitemid 36362757)
4. B Bogdanov RD Smith 2005 Proteomics by FTICR mass spectrometry: top down and bottom up Mass Spectrom Rev 24 2 168 200 1:CAS:528:DC%2BD2MXit1Wgtrk%3D 10.1002/mas.20015 (Pubitemid 40328973)
5. YF Shen RD Smith KK Unger D Kumar D Lubda 2005 Ultrahigh-throughput proteomics using fast RPLC separations with ESI-MS/MS Anal Chem 77 20 6692 6701 1:CAS:528:DC%2BD2MXhtVWnurvM 10.1021/ac050876u (Pubitemid 41504454)
6. NA Mautjana J Estes JR Eyler A Brajter-Toth 2008 Antioxidant pathways and one-electron oxidation of dopamine and cysteine in electrospray and on-line electrochemistry electrospray ionization mass spectrometry Electroanalysis 20 18 1959 1967 1:CAS:528:DC%2BD1cXht1Ojs7bF 10.1002/elan.200804279
7. JR Eyler 2009 Infrared multiple photon dissociation spectroscopy of ions in penning traps Mass Spectrom Rev 28 3 448 467 1:CAS:528:DC%2BD1MXmtVSksr4%3D 10.1002/mas.20217
8. NC Polfer J Oomens 2009 Vibrational spectroscopy of bare and solvated ionic complexes of biological relevance Mass Spectrom Rev 28 3 468 494 1:CAS:528:DC%2BD1MXmtVSksrw%3D 10.1002/mas.20215
9. NA Mautjana J Estes JR Eyler A Brajter-Toth 2008 One-electron oxidation and sensitivity of uric acid in on-line electrochemistry and in electrospray ionization mass spectrometry Electroanalysis 20 23 2501 2508 1:CAS:528:DC%2BD1cXhsFaktL7F 10.1002/elan.200804346
10. NA Mautjana DW Looi JR Eyler A Brajter-Toth 2010 Sensitivity of positive ion mode electrospray ionization mass spectrometry in the analysis of thiol metabolites Electroanalysis 22 1 79 89 1:CAS:528:DC%2BD1MXhs1Wlu7jM
11. NA Mautjana DW Looi JR Eyler A Brajter-Toth 2009 Sensitivity of positive ion mode electrospray ionization mass spectrometry (ESI MS) in the analysis of purine bases in ESI MS and on-line electrochemistry ESI MS (EC/ESI MS) Electrochim Acta 55 1 52 58 1:CAS:528:DC%2BD1MXht1Whu73N 10.1016/j.electacta. 2009.07.083
12. HB Oh C Lin HY Hwang HL Zhai K Breuker V Zabrouskov BK Carpenter FW McLafferty 2005 Infrared photodissociation spectroscopy of electrosprayed ions in a Fourier transform mass spectrometer J Am Chem Soc 127 11 4076 4083 1:CAS:528:DC%2BD2MXhslajsbg%3D 10.1021/ja040136n (Pubitemid 40411449)
13. -1 and theory J Am Chem Soc 131 11 3905 3912 10.1021/ja809928h
14. McLafferty FW (ed) (1983) Tandem mass spectrometry. Wiley, New York
15. Busch KL, Glish GL, McLuckey SA (1988) Mass spectrometry/mass spectrometry: techniques and applications of tandem mass spectrometry. VCH, New York
16. JW Gauthier TR Trautman DB Jacobson 1991 Sustained off-resonance irradiation for collision-activated dissociation involving Fourier transform mass spectrometry collision-activated dissociation technique that emulates infrared multiphoton dissociation Anal Chim Acta 246 1 211 225 1:CAS:528:DyaK3MXkslSkurw%3D 10.1016/S0003-2670(00)80678-9
17. + structures on the basis of chemical reactivity J Am Chem Soc 103 21 6505 6507 1:CAS:528:DyaL3MXmtVejsbc%3D 10.1021/ja00411a045
18. DD Fetterolf RA Yost JR Eyler 1984 The use of reactive collisions in tandem mass spectrometry for the differentiation of isomeric structures Org Mass Spectrom 19 2 104 105 1:CAS:528:DyaL2cXlslSnurc%3D 10.1002/oms.1210190212
19. M Green C Lebrilla 1997 Ion-molecule reactions as probes of gas-phase structures of peptides and proteins: dedicated to the memory of Professor RW Taft Mass Spectrom Rev 16 2 53 57 1:CAS:528:DyaK2sXmsF2js70%3D 10.1002/(SICI)1098-2787(1997)16:2<53::AID-MAS1>3.0.CO;2-8
20. J Atzrodt V Derdau T Fey J Zimmermann 2007 The renaissance of H/D exchange Angew Chem Int Ed 46 41 7744 7765 1:CAS:528:DC%2BD2sXht1alsL3M 10.1002/anie.200700039 (Pubitemid 47612897)
21. Parr RG (ed) (1995) Density-functional theory of atoms and molecules. Oxford University Press, Oxford
22. Koch W, Holthausen MC (2001) A chemist's guide to density functional theory, 2nd edn. Wiley, Weinheim
23. M Alcami O Mo M Yanez 2002 Computational chemistry: a useful (sometimes mandatory) tool in mass spectrometry studies Mass Spectrom Rev 20 4 195 245 10.1002/mas.10005
24. J Oomens BG Sartakov G Meijer G von Helden 2006 Gas-phase infrared multiple photon dissociation spectroscopy of mass-selected molecular ions Int J Mass Spectrom 254 1-2 1 19 1:CAS:528:DC%2BD28XmslGqtbg%3D
25. TD Fridgen 2009 Infrared consequence spectroscopy of gaseous protonated and metal ion cationized complexes Mass Spectrom Rev 28 4 586 607 1:CAS:528:DC%2BD1MXos1Whs7Y%3D 10.1002/mas.20224
26. Oomens J, Tielens AGGM, Sartakov BG, von Helden G, Meijer G (2003) Laboratory infrared spectroscopy of cationic polycyclic aromatic hydrocarbon molecules. Astrophys J 591 (2, Pt. 1):968-985 (Pubitemid 37195172)
27. D Oepts AFG Vandermeer PW Vanamersfoort 1995 The free-electron-laser user facility FELIX Infrared Phys Technol 36 1 297 308 1:CAS:528:DyaK2MXltlCksrg%3D 10.1016/1350-4495(94)00074-U
28. R Prazeres F Glotin C Insa DA Jaroszynski JM Ortega 1998 Two-color operation and applications of the CLIO FEL in the mid-infrared range Nucl Instrum Methods Phys Res, Sect A 407 1-3 464 469 1:CAS:528:DyaK1cXjvVWhs7s%3D 10.1016/S0168-9002(98)00069-2 (Pubitemid 128409331)
29. R Prazeres F Glotin JM Ortega 2004 New results of the 'CLIO' infrared FEL Nucl Instrum Methods Phys Res, Sect A 528 1-2 83 87 1:CAS:528: DC%2BD2cXmt1Cluro%3D 10.1016/j.nima.2004.04.023
30. Y Choi DM Lubman 1992 Analytical spectroscopy and structure of biomolecules using an ab initio computational method Anal Chem 64 22 2726 2734 1:CAS:528:DyaK38XmtFWkt7w%3D 10.1021/ac00046a014 (Pubitemid 23003633)
31. NA Macleod JP Simons 2006 Infrared photodissociation spectroscopy of protonated neurotransmitters in the gas phase Mol Phys 104 20-21 3317 3328 1:CAS:528:DC%2BD2sXhtVajsr8%3D 10.1080/00268970601110340 (Pubitemid 47226469)
32. JC Dobrowolski MH Jamroz R Kolos JE Rode J Sadlej 2007 Theoretical prediction and the first IR matrix observation of several L-cysteine molecule conformers Chemphyschem 8 7 1085 1094 1:CAS:528:DC%2BD2sXlvVGksrY%3D 10.1002/cphc.200600784
33. H Lioe RAJ O'Hair 2007 Comparison of collision-induced dissociation and electron-induced dissociation of singly protonated aromatic amino acids, cystine and related simple peptides using a hybrid linear ion trap-FT-ICR mass spectrometer Anal Bioanal Chem 389 5 1429 1437 1:CAS:528:DC%2BD2sXht1GhsL3I 10.1007/s00216-007-1535-1 (Pubitemid 350023667)
34. ME Sanz S Blanco JC Lopez JL Alonso 2008 Rotational probes of six conformers of neutral cysteine Angew Chem Int Ed 47 33 6216 6220 1:CAS:528:DC%2BD1cXpvFSgt7g%3D 10.1002/anie.200801337
35. JJ Wilke MC Lind HF Schaefer AG Csaszar WD Allen 2009 Conformers of gaseous cysteine J Chem Theory Comput 5 6 1511 1523 1:CAS:528: DC%2BD1MXlvFCrsb4%3D 10.1021/ct900005c
36. S Pande S Jana AK Sinha S Sarkar M Basu M Pradhan A Pal J Chowdhury T Pal 2009 Dopamine molecules on Au-core-Ag-shell bimetallic nanocolloids: Fourier transform infrared, Raman, and surface-enhanced Raman spectroscopy study aided by density functional theory J Phys Chem C 113 17 6989 7002 1:CAS:528: DC%2BD1MXktFOjtLw%3D 10.1021/jp810210a
37. DCS Tse RL McCreery RN Adams 1976 Potential oxidative pathways of brain catecholamines J Med Chem 19 1 37 40 1:CAS:528:DyaE28XjvFSgsg%3D%3D 10.1021/jm00223a008
38. GR Buettner 1993 The pecking order of free-radicals and antioxidants-lipid-peroxidation, alpha-tocopherol, and ascorbate Arch Biochem Biophys 300 2 535 543 1:CAS:528:DyaK3sXpsFKkug%3D%3D 10.1006/abbi.1993.1074 (Pubitemid 23232908)
39. Voet D, Voet JG (1990) Biochemistry. Wiley, New York
40. WE Funk H Li AT Iavarone ER Williams J Riby SM Rappaport 2010 Enrichment of cysteinyl adducts of human serum albumin Anal Biochem 400 1 61 68 1:CAS:528:DC%2BC3cXjtVClsLY%3D 10.1016/j.ab.2010.01.006
41. EE Battin JL Brumaghim 2009 Antioxidant activity of sulfur and selenium: a review of reactive oxygen species scavenging, glutathione peroxidase, and metal-binding antioxidant mechanisms Cell Biochem Biophys 55 1 1 23 1:CAS:528:DC%2BD1MXosV2ksL8%3D 10.1007/s12013-009-9054-7
42. AC Hopkinson 2009 Radical cations of amino acids and peptides: structures and stabilities Mass Spectrom Rev 28 4 655 671 1:CAS:528:DC%2BD1MXos1WhsL8%3D 10.1002/mas.20229
43. RH Wu TB McMahon 2008 An investigation of protonation sites and conformations of protonated amino acids by IRMPD spectroscopy Chemphyschem 9 18 2826 2835 1:CAS:528:DC%2BD1MXnsFyjsw%3D%3D 10.1002/cphc.200800543
44. J Zhao KWM Siu AC Hopkinson 2008 The cysteine radical cation: structures and fragmentation pathways Phys Chem Chem Phys 10 2 281 288 1:CAS:528: DC%2BD1cXhtVGksLw%3D 10.1039/b712628j
45. NIST Chemistry Webbook (2008) http://webbook.nist.gov/chemistry.
46. JF Zhao CMD Ng IK Chu KWM Siu AC Hopkinson 2009 Methionine, alpha-methylmethionine and S-methylcysteine radical cations: generations and dissociations in the gas phase Phys Chem Chem Phys 11 35 7629 7639 1:CAS:528:DC%2BD1MXhtVGgsrfJ 10.1039/b905615g
47. V Ryzhov AKY Lam RAJ O'Hair 2009 Gas-phase fragmentation of long-lived cysteine radical cations formed via NO loss from protonated S-nitrosocysteine J Am Soc Mass Spectrom 20 6 985 995 1:CAS:528:DC%2BD1MXmtVegs7c%3D 10.1016/j.jasms.2008.12.026
48. BS Jursic 1997 Computation of bond dissociation energy for sulfides and disulfides with ab initio and density functional theory methods Int J Quantum Chem 62 3 291 296 1:CAS:528:DyaK2sXhvVyjtLw%3D 10.1002/(SICI)1097-461X(1997)62: 3<291::AID-QUA7>3.0.CO;2-R (Pubitemid 127549796)
49. AB McCoy JL Fry JS Francisco AK Mollner M Okumura 2005 Role of OH-stretch/torsion coupling and quantum yield effects in the first OH overtone spectrum of cis-cis HOONO J Chem Phys 122 10 1043111 10431114 10.1063/1.1859273 (Pubitemid 40536565)
50. J Oomens JD Steill B Redlich 2009 Gas-phase ir spectroscopy of deprotonated amino acids J Am Chem Soc 131 12 4310 4319 1:CAS:528: DC%2BD1MXislOjtb0%3D 10.1021/ja807615v
51. WJ Barreto S Ponzoni P Sassi 1999 A Raman and UV-VIS study of catecholamines oxidized with Mn(III) Spectrochim Acta A 55 1 65 72 (Pubitemid 128411884)
52. PI Nagy G Alagona C Ghio 1999 Theoretical studies on the conformation of protonated dopamine in the gas phase and in aqueous solution J Am Chem Soc 121 20 4804 4815 1:CAS:528:DyaK1MXivVaksbo%3D 10.1021/ja981528v (Pubitemid 29252634)
53. JJ Urban CJ Cramer GR Famini 1992 A computational study of solvent effects on the conformation of dopamine J Am Chem Soc 114 21 8226 8231 1:CAS:528:DyaK38XlslWktL0%3D 10.1021/ja00047a037
54. P Carcabal LC Snoek T Van Mourik 2005 A computational and spectroscopic study of the gas-phase conformers of adrenaline Mol Phys 103 11-12 1633 1639 1:CAS:528:DC%2BD2MXkvVOmsLk%3D 10.1080/00268970500086039 (Pubitemid 41657176)