Consecutive fragmentation mechanisms of protonated ferulic acid probed by infrared multiple photon dissociation spectroscopy and electronic structure calculations

Journal of the American Society for Mass Spectrometry

Volumn 23, Issue 10, 2012, Pages 1697-1706

  Martens, Sabrina M ^a   Marta, Rick A ^a   Martens, Jonathan K ^a   McMahon, Terry B ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Density functional theory; Energetics; Ferulic acid; Free electron laser; Gas phase fragmentation; Ion structure; IRMPD; Vibrational spectra

Indexed keywords

ENERGETICS; FERULIC ACIDS; GAS-PHASE FRAGMENTATION; ION STRUCTURES; IRMPD;

CARBON MONOXIDE; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRONIC STRUCTURE; FREE ELECTRON LASERS; IONS; METHANOL; PHOTONS; PROTON TRANSFER; VIBRATIONAL SPECTRA;

PROTONATION;

CARBON MONOXIDE; FERULIC ACID; METHANOL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRONIC STRUCTURE CALCULATION; ELECTRONICS; FRAGMENTATION REACTION; INFRARED MULTIPLE PHOTON DISSOCIATION SPECTROSCOPY; PROTON TRANSPORT; REACTION ANALYSIS; REACTION OPTIMIZATION; SPECTROSCOPY; STRUCTURE ANALYSIS; THEORETICAL STUDY; WATER LOSS;

CARBON MONOXIDE; COUMARIC ACIDS; GASES; IONS; ISOMERISM; MASS SPECTROMETRY; METHANOL; THERMODYNAMICS;

EID: 84868218130     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-012-0438-3     Document Type: Article

References (43)

1. Mathew, S., Abraham, T.E.: Ferulic Acid: an antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications. Crit. Rev. Biotechnol. 24, 59-83 (2004)
2. Iiyama, K., Lam, T.B.T., Stone, B.A.: Covalent cross-links in the cell wall. Plant Physiol. 104, 315-320 (1994)
3. Casolaro, M., Anselmi, C., Picciocchi, G.: The protonation thermodynamics of ferulic acid/[gamma]-cyclodextrin inclusion compounds. Thermochim. Acta 425, 143-147 (2005)
4. Kikuzaki, H., Hisamoto, M., Hirose, K., Akiyama, K., Taniguchi, H.: Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 50, 2161-2168 (2002)
5. Graf, E.: Antioxidant potential of ferulic acid. Free Radic. Biol. Med. 13, 435-448 (1992)
6. Maurya, D.K., Devasagayam, T.P.A.: Antioxidant and pro-oxidant nature of hydroxycinnamic acid derivatives ferulic and caffeic acids. Food Chem. Toxicol. 48, 3369-3373 (2010)
7. Riemer, J.A.: Bitterness inhibitors. United States Patent. Kraft General Foods, Inc., USA (1993)
8. Marta, R.A., Wu, R.H., Eldridge, K.R., Martens, J.K., McMahon, T.B.: The sodium cation-bound dimer of theophylline: IRMPD spectroscopy of a highly symmetric electrostatically bound species. Int. J. Mass Spectrom. 297, 76-84 (2010)
9. Schafer, M., Drayss, M.K., Blunk, D., Purcell, J.M., Hendrickson, C.L., Marshall, A.G., Mookherjee, A., Armentrout, P.B.: Kinetic determination of potassium affinities by IRMPD: elucidation of precursor ion structures. J. Phys. Chem. A 113, 7779-7783 (2009)
10. O'Brien, J.T., Prell, J.S., Berden, G., Oomens, J., Williams, E.R.: Effects of anions on the zwitterion stability of Glu, His, and Arg investigated by IRMPD spectroscopy and theory. Int. J. Mass Spectrom. 297, 116-123 (2010)
11. Dunbar, R.C., Steill, J.D., Oomens, J.: Cationized phenylalanine conformations characterized by IRMPD and computation for singly and doubly charged ions. Phys. Chem. Chem. Phys. 12, 13383-13393 (2010)
12. Wu, R., Marta, R., Martens, J., Eldridge, K., McMahon, T.: Experimental and theoretical investigation of the proton-bound dimer of lysine. J. Am. Soc. Mass Spectrom. 22, 1651-1659 (2011)
13. Martens, S.M., Marta, R.A., Martens, J.K., McMahon, T.B.: Tridentate ionic hydrogen-bonding interactions of the 5-fluorocytosine cationic dimer and other 5-fluorocytosine analogues characterized by IRMPD spectroscopy and electronic structure calculations. J. Phys. Chem. A 115, 9837-9844 (2011)
14. Marta, R.A., McMahon, T.B., Fridgen, T.D.: Infrared multiphoton dissociation spectra as a probe of ion molecule reaction mechanism: the formation of the protonated water dimer via sequential bimolecular reactions with 1,1,3,3-tetrafluorodimethyl ether. J. Phys. Chem. A 111, 8792-8802 (2007)
15. Wu, R.H., McMahon, T.B.: Infrared multiple photon dissociation spectroscopy as structural confirmation for GlyGlyGlyH(+) and AlaAlaAlaH(+) in the gas phase. Evidence for amide oxygen as the protonation site. J. Am. Chem. Soc. 129, 11312 (2007)
16. Wu, R.H., McMahon, T.B.: An investigation of protonation sites and conformations of protonated amino acids by IRMPD spectroscopy. Chem. Phys. Chem. 9, 2826-2835 (2008)
17. Fridgen, T.D.: Infrared consequence spectroscopy of gaseous protonated and metal ion cationized complexes. Mass Spectrom. Rev. 28, 586-607 (2009)
18. Rajabi, K., Theel, K., Gillis, E.A.L., Beran, G., Fridgen, T.D.: The Structure of the protonated adenine dimer by infrared multiple photon dissociation spectroscopy and electronic structure calculations. J. Phys. Chem. A 113, 8099-8107 (2009)
19. Rizzo, T.R., Stearns, J.A., Boyarkin, O.V.: Spectroscopic studies of cold, gas-phase biomolecular ions. Int. Rev. Phys. Chem. 28, 481-515 (2009)
20. Stearns, J.A., Seaiby, C., Boyarkin, O.V., Rizzo, T.R.: Spectroscopy and conformational preferences of gas-phase helices. Phys. Chem. Chem. Phys. 11, 125-132 (2009)
21. Wu, R.H., McMahon, T.B.: Protonation sites and conformations of peptides of glycine [Gly(1-5)H(+)] by IRMPD Spectroscopy. J. Phys. Chem. B 113, 8767-8775 (2009)
22. Drayss, M.K., Armentrout, P.B., Oomens, J., Schaefer, M.: IR spectroscopy of cationized aliphatic amino acids: stability of charge-solvated structure increases with metal cation size. Int. J. Mass Spectrom. 297, 18-27 (2010)
23. Gillis, E.A.L., Fridgen, T.D.: The hydrated Li(+)-adenine-thymine complex by IRMPD spectroscopy in the N-H/O-H stretching region. Int. J. Mass Spectrom. 297, 2-8 (2010)
24. Marta, R.A., Wu, R.H., Eldridge, K.R., Martens, J.K., McMahon, T.B.: Infrared vibrational spectra as a structural probe of gaseous ions formed by caffeine and theophylline. Phys. Chem. Chem. Phys. 12, 3431-3442 (2010)
25. Mino, W.K., Szczepanski, J., Pearson, W.L., Powell, D.H., Dunbar, R.C., Eyler, J.R., Polfer, N.C.: Vibrational signatures of zwitterionic and charge-solvated structures for alkaline earth-tryptophan dimer complexes in the gas phase. Int. J. Mass Spectrom. 297, 131-138 (2010)
26. Prell, J.S., Flick, T.G., Oomens, J., Berden, G., Williams, E.R.: Coordination of trivalent metal cations to peptides: results from IRMPD spectroscopy and theory. J. Phys. Chem. A 114, 854-860 (2010)
27. Rajabi, K., Gillis, E.A.L., Fridgen, T.D.: Structures of alkali metal ionadenine complexes and hydrated complexes by IRMPD spectroscopy and electronic structure calculations. J. Phys. Chem. A 114, 3449-3456 (2010)
28. Semrouni, D., Balaj, O.P., Calvo, F., Correia, C.F., Clavaguera, C., Ohanessian, G.: Structure of sodiated octa-glycine: IRMPD spectroscopy and molecular modeling. J. Am. Soc. Mass Spectrom. 21, 728-738 (2010)
29. Dunbar, R.C., Steill, J.D., Oomens, J.: Encapsulation of metal cations by the PhePhe ligand: a cation-pi ion cage. J. Am. Chem. Soc. 133, 9376-9386 (2011)
30. Dunbar, R.C., Steill, J.D., Oomens, J.: Chirality-induced conformational preferences in peptide-metal ion binding revealed by IR spectroscopy. J. Am. Chem. Soc. 133, 1212-1215 (2011)
31. Ortega, J.M., Glotin, F., Prazeres, R.: Extension in far-infrared of the CLIO free-electron laser. Infrared Phys. Technol. 49, 133-138 (2006)
32. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F.J., Bloino, G.Z., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B.J.V., Ortiz, J.C., Fox, D.J.: Gaussian 09, Revision A. 02. Gaussian, Inc, Wallingford (2009)
33. Carl, D.R., Cooper, T.E., Oomens, J., Steill, J.D., Armentrout, P.B.: Infrared multiple photon dissociation spectroscopy of cationized methionine: effects of alkali-metal cation size on gas-phase conformation. Phys. Chem. Chem. Phys. 12, 3384-3398 (2010)
34. Armentrout, P.B., Rodgers, M.T., Oomens, J., Steill, J.D.: Infrared multiphoton dissociation spectroscopy of cationized serine: effects of alkali-metal cation size on gas-phase conformation. J. Phys. Chem. A 112, 2248-2257 (2008)
35. Cooper, T.E., Carl, D.R., Oomens, J., Steill, J.D., Armentrout, P.B.: Infrared spectroscopy of divalent zinc and cadmium crown ether systems. J. Phys. Chem. A 115, 5408-5422 (2011)
36. Dunbar, R.C., Steill, J.D., Oomens, J.: Conformations and vibrational spectroscopy of metal-ion/polylalanine complexes. Int. J. Mass Spectrom. 297, 107-115 (2010)
37. Andersson, M.P., Uvdal, P.: New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-xi basis set 6-311+G(d, p). J. Phys. Chem. A 109, 2937-2941 (2005)
38. Barone, V.: Vibrational zero-point energies and thermodynamic functions beyond the harmonic approximation. J. Chem. Phys. 120, 3059-3065 (2004)
39. Clabo Jr., D.A., Allen, W.D., Remington, R.B., Yamaguchi, Y., Schaefer III, H.F.: A systematic study of molecular vibrational anharmonicity and vibration-rotation interaction by SCF higher-derivative methods. Asymmetric top Molecules. Chem. Phys. 123, 187-239 (1988)
40. CRC Handbook of Chemistry and Physics. Cleavland, Ohio: The Chemical Rubber Co. (1971)
41. Gardner, M., Li, N., Ellington, A., Brodbelt, J.: Infrared multiphoton dissociation of small-interfering RNA anions and cations. J. Am. Soc. Mass Spectrom. 21, 580-591 (2010)
42. Surjasasmita, P.I., Freiser, B.S.: Collision-induced and infrared multiphoton dissociation studies on M(acetone)2+ (M=A1, Fe, Co, Cu, ScO) in the gas phase. J. Am. Soc. Mass Spectrom. 4, 135-144 (1993)
43. Parr, C., Brodbelt, J.S.: Increased sequence coverage of thymine-rich oligodeoxynucleotides by infrared multiphoton dissociation compared to collision-induced dissociation. J. Mass Spectrom. 45, 1098-1103 (2010)