Differentiation of regioisomeric aromatic ketocarboxylic acids by positive mode atmospheric pressure chemical ionization collision-activated dissociation tandem mass spectrometry in a linear quadrupole ion trap mass spectrometer

Journal of the American Society for Mass Spectrometry

Volumn 22, Issue 4, 2011, Pages 670-682

  Amundson, Lucas M ^a   Owen, Benjamin C ^a   Gallardo, Vanessa A ^a   Habicht, Steven C ^a,c   Fu, Mingkun ^a,d   Shea, Ryan C ^b   Mossman, Allen B ^b   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

^b BP AMERICA INC   (United States)

^c Center for Naval Analysis   (United States)

^d MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

Aromatic carboxylic acids; Atmospheric pressure chemical ionization; Regioisomers; Tandem mass spectrometry

Indexed keywords

ANALYTES; APCI-MS; AROMATIC CARBOXYLIC ACIDS; ATMOSPHERIC PRESSURE CHEMICAL IONIZATION; COLLISION ENERGIES; COLLISION-ACTIVATED DISSOCIATIONS; FRAGMENT IONS; FRAGMENTATION PATTERNS; H/D EXCHANGE REACTIONS; ION-MOLECULE REACTION; KETOCARBOXYLIC ACIDS; LINEAR QUADRUPOLE ION TRAPS; MOLECULAR ORBITAL CALCULATIONS; POSITIVE MODE; PROTONATED; PROTONATED MOLECULES; REGIOISOMERS; RELATIVE ABUNDANCE; TANDEM MASS SPECTROMETRY;

AROMATIC COMPOUNDS; AROMATIZATION; ATMOSPHERIC CHEMISTRY; ATMOSPHERIC PRESSURE; ATMOSPHERICS; CARBOXYLIC ACIDS; CHEMICAL ANALYSIS; DISSOCIATION; DRUG PRODUCTS; FUNCTIONAL GROUPS; IONIZATION; IONS; MASS SPECTROMETERS; MASS SPECTROMETRY; MOLECULAR ORBITALS; PROTONATION;

ATMOSPHERIC IONIZATION;

AROMATIC CARBOXYLIC ACID; AROMATIC KETOCARBOXYLIC ACID; FUNCTIONAL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLLISIONALLY ACTIVATED DISSOCIATION; ENERGY; FRAGMENTATION REACTION; ION EXCHANGE; ION TRAP MASS SPECTROMETRY; IONIZATION; ISOMER; MATHEMATICAL COMPUTING; POSITIVE MODE ATMOSPHERIC PRESSURE CHEMICAL IONIZATION TANDEM MASS SPECTROMETRY; PROTON TRANSPORT; TANDEM MASS SPECTROMETRY;

ATMOSPHERIC PRESSURE; BENZOIC ACIDS; CARBOXYLIC ACIDS; FLUORENES; KETONES; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; WATER;

EID: 79955762954     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0079-y     Document Type: Article

References (37)

1. Chang, M.C.Y.: Harnessing energy from plant biomass. Curr. Opin. Chem. Bio. 11, 677-684 (2007)
2. Ragauskas, A.J., Williams, C.K., Davison, B.H., Britovsek, G., Cairney, J., Eckert, C.A., Frederick Jr., W.J., Hallett, J.P., Leak, D.J., Liotta, C. L., Mielenz, J.R., Murphy, R., Templer, R., Tschaplinski, T.: The path forward for biofules and biomaterials. Science 311, 484-489 (2006)
3. Weng, J.-K., Li, X., Bonawitz, N.D., Chapple, C.: Emerging strategies of lignin engineering and degradation for cellulosic biofuel production. Curr. Opin. Biotech. 19, 166-172 (2008)
4. Zakzeski, J., Bruijnincx, P.C.A., Jongerius, A.L., Weckhuysen, B.M.: The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 110, 3552-3599 (2010)
5. Hamelinck, C.N., Hooijdonk, G., Faaij, A.P.C.: Ethanol from lignocellulosic biomass: Techno-economic performance in short-, middle-, and long-term. Biomass Bioenergy 28, 384-410 (2005)
6. Li, X., Weng, J.-K., Chapple, C.: Improvement of biomass through lignin modification. Plant J. 54, 569-581 (2008) (Pubitemid 351678045)
7. Hisano, H., Nandakumar, R., Wang, Z.-Y.: Genetic modification of lignin biosynthesis for improved biofuel production. In Vitro Cell. Dev. Biol Plant. 45, 306-313 (2009)
8. Habicht, S.C., Vinueza, N.R., Archibold, E.F., Duan, P., Kenttämaa, H.I.: Identification of the carboxylic acid functionality by using electrospray ionization and ion-molecule reactions in a modified linear quadrupole ion trap mass spectrometer. Anal. Chem. 80, 3416-3421 (2008) (Pubitemid 351620729)
9. Lecchi, P., Zhao, J., Wiggins, W.S., Chen, T.-C., Yip, P.F., Mansfield, B. C., Peltier, J.M.: A method for monitoring and controlling reproducibility of intensity data in complex electrospray mass spectra: A thermometer ionbased strategy. J. Am. Soc. Mass Spectrom. 20, 398-410 (2009)
10. Ma, S., Chowdhury, S.K., Alton, K.B.: Application of mass spectrometry for metabolite identification. Curr. Drug Metab. 7, 503-523 (2006)
11. Prakash, C., Schaffer, C.L., Nedderman, A.: Analytical strategies for identifying drug metabolites. Mass Spectrom. Rev. 26, 340-369 (2007) (Pubitemid 46750374)
12. Catarina, I.V.R., Santana-Marques, M.G., Roger, F.E., Augusto, C.T., José, A.S.C., Manuel, N.: Gas-phase fragmentation of protonated C60- pyrimidine derivatives. J. Mass Spectrom. 44, 911-919 (2009)
13. Kolakowski, B.M., Grossert, J.S., Ramaley, L.: The importance of both charge exchange and proton transfer in the analysis of polycyclic aromatic compounds using atmospheric pressure chemical ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 15, 301-310 (2004) (Pubitemid 38283875)
14. Ramesh, M., Ramesh, V., Raju, B., Srinivas, R., Kumaraswamy, G., Markondaiah, B., Padmaja, M.: Diastereomeric differentiation of oppolzer sultam derivatives using electrospray ionization and atmospheric pressure photoionization tandem mass spectrometry. J. Mass Spectrom. 44, 1114-1118 (2009)
15. Ramesh, V., Srinivas, R., Kumaraswamy, G., Markondaiah, B.: Diastereoselectivity in the McLafferty-type rearrangement of protonated precursors of belactosin derivatives using electrospray ionization (ESI) and Atmospheric Pressure Photoionization (APPI) tandem mass spectrometry. J. Mass Spectrom. 44, 285-287 (2009)
16. Witt, M., Fuchser, J., Koch, B.P.: Fragmentation studies of fulvic acids using collision induced dissociation fourier transform ion cyclotron resonance mass spectrometry. Anal. Chem. 81, 2688-2694 (2009)
17. Yanchun, G., Shuxia, C., Donghui, W., Xiangkun, Z., Xingbo, Y., Mingsheng, T., Yufen, Z.: Fragmentation of deprotonated cyclic dipeptides by electrospray ionization mass spectrometry. J. Mass Spectrom. 44, 1188-1194 (2009)
18. Ying, L., Jiuming, H., Ruiping, Z., Jiangong, S., Zeper, A.: Study of the characteristic fragmentation behavior of hydroquinone glycosides by electrospray ionization tandem mass spectrometry with optimization of collision energy. J. Mass Spectrom. 44, 1182-1187 (2009)
19. Donovan, T., Brodbelt, J.: Selective ion molecule reactions of 2, 5- dimethylpyrrole-γ-butyrolactone with dimethyl ether ions. Bio. Mass Spectrom. 21, 254-258 (1992)
20. Smith, R.J., Webb, M.I. (eds): Analysis of Drug Impurities; Blackwell Publishing: Oxford, UK, 2007
21. Palit, M., Mallard, G.: Fragmentation energy index for universalization of fragmentation energy in ion trap mass spectrometers for the analysis of chemical weapon convention related chemicals by atmospheric pressure ionization-tandem mass spectrometry analysis. Anal. Chem. 81, 2477-2485 (2009)
22. Biemann, K.: Mass spectrometry of peptides and proteins. Annu. Rev. Biochem. 61, 977-1010 (1992)
23. Badjagbo, K., Picard, P., Moore, S., Sauvé, S.: Direct atmospheric pressure chemical ionization-tandem mass spectrometry for the continuous real-time trace analysis of benzene, toluene, ethylbenzene, and xylenes in ambient air. J. Am. Soc. Mass Spectrom. 20, 829-836 (2009)
24. Auld, J., Hastie, D.R.: Tandem mass spectrometry and multiple reaction monitoring using an atmospheric pressure chemical ionization triple quadrupole mass spectrometer for product identification in atmospherically important reactions. Int. J. Mass Spectrom. 282, 91-98 (2009)
25. Cao, H., Wang, Y.: Fragmentation of isomeric intrastrand crosslink lesions of DNA in an ion-trap mass spectrometer. J. Am. Soc. Mass Spectrom. 20, 611-617 (2009)
26. Vooturi, S.K., Cheung, C.M., Rybak, M.J., Firestine, S.M.: Design, synthesis, and structure-activity relationships of benzophenone-based tetra-amides as novel antibacterial agents. J. Med. Chem. 52, 5020-5031 (2009)
27. Negreira, N., Rodríguez, I., Ramil, M., Rubí, R.C.: Sensitive determination of salicylate and benzophenone type UV filters in water samples using solid-phase microextraction, derivatization and gas chromatography tandem mass spectrometry. Anal. Chim. Acta 638, 36-44 (2009)
28. Davies, N.W., Smith, J.A., Molesworth, P.P., Ross, J.J.: Hydrogen/ Deuterium exchange on aromatic rings during atmospheric pressure chemical ionization mass spectrometry. Rapid Comm. Mass Spectrom. 24, 1105-1110 (2010)
29. Fabrice, C., Dominique, B.-R., Saïd, Y., Catherine, M., Daniel, J., Monique, G.-A.: Online H/D exchange liquid chromatography as a support for the mass spectrometric identification of the oxidation products of melatonin. J. Mass Spectrom. 44, 318-329 (2009)
30. Fu, M., Duan, P., Li, S., Eismin, R.J., Kenttämaa, H.I.: An Ion/ Molecule reaction for the identification of analytes with two basic functional groups. 20, 1251-1262 (2009)
31. Choe, J.C., Cheong, N.R., Park, S.M.: Unimolecular dissociation of aniline molecular ion: A theoretical study. Int. J. Mass Spectrom. 279, 25-31 (2009)
32. Eduardo, A.S.E., Wilmer, E.V.N.: Density functional theory and RRKM calculations of the gas-phase unimolecular rearrangements of methylfuran and pyran ions before fragmentations. J. Mass Spectrom. 44, 1452-1458 (2009)
33. Bandu, M.L., Watkins, K.R., Bretthauer, M.L., Moore, C.A., Desaire, H.: Prediction of MS/MS Data. 1. A focus on pharmaceuticals containing carboxylic acids. Anal. Chem. 76, 1746-1753 (2004) (Pubitemid 38338424)
34. Schug, K., McNair, H.M.: Adduct formation in electrospray ionization. Part 1: Common acidic pharmaceuticals. J. Sep. Sci. 25, 760-766 (2002) (Pubitemid 35021582)
35. Schug, K., McNair, H.M.: Adduct formation in electrospray ionization mass spectrometry II. Benzoic Acid Derivatives. J. Chromatogr. A 985, 531-539 (2003) (Pubitemid 36164843)
36. Lopez, L.L., Tiller, P.R., Senko, M.W., Schwartz, J.C.: Automated strategies for obtaining standardized collisionally induced dissociation spectra on a benchtop ion trap mass spectrometer. Rapid Commun. Mass Spectrom. 13, 663-668 (1999) (Pubitemid 29194452)
37. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M. A., Cheeseman, J.R., Montgomery, J.A.J., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, B., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., 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., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J. J., Zarzewski, V.G., Dap-Prich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghayachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A.: Gaussian 03, Revision C.02 2004 Gaussian, Inc.: Wallingford, CT, (2004)