Derivatization in mass spectrometry - 7. On-line derivatization/degradation

European Journal of Mass Spectrometry

Volumn 12, Issue 1, 2006, Pages 1-13

  Halket, John M ^a   Zaikin, Vladimir G ^b  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b TOPCHIEV INSTITUTE OF PETROCHEMICAL SYNTHESIS   (Russian Federation)

Author keywords

Acylation; Deuteration; DP MS; Esterification; In flash heater derivatization; On column derivatization; Oxidation; Polymers; Post column derivatization; Pre column derivatization; Py GC MS; Py MS; Silylation; Unsaturated compounds

Indexed keywords

EID: 33645913262     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.785     Document Type: Review

References (80)

1. J.M. Halket and V.G. Zaikin, "Derivatization in mass spectrometry-1. Silylation", Eur. J. Mass Spectrom. 9, 1 (2003). doi: 10.1255/ejms.527
2. V.G. Zaikin and J.M. Halket, "Derivatization in mass spectrometry-2. Acylation", Eur. J. Mass Spectrom. 9, 421 (2003). doi: 10.1255/ejms.576
3. J.M. Halket and V.G. Zaikin, "Derivatization in mass spectrometry-3. Alkylation(arylation)", Eur. J. Mass Spectrom. 10, 1 (2004). doi: 10.1255/ejms.619
4. V.G. Zaikin and J.M. Halket, "Derivatization in mass spectrometry-4. Formation of cyclic derivatives", Eur. J. Mass Spectrom. 10, 555 (2004). doi: 10.1255/ejms.653
5. J.M. Halket and V.G. Zaikin, "Derivatization in mass spectrometry-5. Specific derivatization of monofunctional compounds", Eur. J. Mass Spectrom. 11, 127 (2005). doi: 10.1255/ejms.712
6. V.G. Zaikin and J.M. Halket, "Derivatization in mass spectrometry-6. Mixed derivatization", Eur. J. Mass Spectrom. 11, 611 (2005). doi: 10.1255/ejms.773
7. th ASMS Conference on Mass Spectrometry and Allied Topics, San Francisco, 167 (1988).
8. A.I. Mikaya and V.G. Zaikin, "Reaction gas chromatography/mass spectrometry", Mass Spectrom. Rev. 9, 115 (1990). doi: 10.1002/mas. 1280090105
9. V.G. Berezkin, Chemical Methods in Gas Chromatography. Elsevier, Amsterdam, The Netherlands (1983).
10. T.S. Ma and A.S. Ladas, Organic Functional Group Analysis by Gas Chromatography. Academic Press, London, UK (1976).
11. A.A. Polyakova, Molecular Mass Spectral Analysis of Organic Compounds, (Russian). Khimija, Moscow, Russia (1983).
12. G. Montaudo and C. Puglisi, "Direct pyrolysis into the ion source of a mass spectrometer (DP-MS)", in Mass Spectrometry of Polymers, Ed by G. Montaudo and R.P. Lattimer. CRC Press, Boca Raton, FL, USA, p. 181 (2002).
13. G. Montaudo and R.P. Lattimer (Eds.), Mass Spectrometry of Polymers, CRC Press, Boca Raton, FL, USA (2002).
14. C.-H. Liu and W.-H. Ding, "Determination of naphthalenesulfonic acid isomers by large-volume on-line derivatization and gas chromatography-mass spectrometru", J. Chromatogr. A 926, 341 (2001). doi: 10.1016/S0021- 9673(01)01075-5
15. R. Osiewicz, V. Aggarwal, R.M. Young and I. Sunshine, "Quantitative analysis of phenobarbital with trimethylanilinium hydroxide", J. Chromatogr. 88, 157 (1974). doi: 10.1016/S0021-9673(01)91780-7
16. R. Alzagaand J.M. Bayona "Determination of perfluorocarboxylic acids in aqueous matrices by ion-pair solid phase microextraction-in-port derivatization-gas chromatography-negative ion chemical ionization mass spectrometry", J. Chromatogr. A 1042, 155 (2004). doi: 10.1016/j.chroma. 2004.05.015
17. D. Fabbri, V. Baravelli, G. Chiavari and S. Prati, "Dimethyl carbonate as a novel methylating reagent for fatty acids in analytical pyrolysis", J. Chromatogr. A 1065, 257 (2005). 10.1016/j.chroma.2004.12.077
18. Y. Hasegawa, Y. Maruyama and S.T. Weintraub, "A new look at the mechanism of chemical ionization fragmentation of demethylated choline esters", Biomed. Mass Spectrom. 11, 315 (1984). 10.1002/bms.1200110702
19. W.B. Stavinoha and S.T. Weintraub, "Estimation of choline and acetylcholine in tissue by pyrolysis gas chromatography", Anal. Chem. 46, 757 (1974). doi: 10.1021/ac60342a042
20. W. Danildewicz, K. Wojchechowski and M. Olejnik, "Preparation and reactions of aza-ortho-xylylenes in the injection of GC/MS system", Tetrahedron Lett. 30, 1099 (1995). doi: 10.1016/0040-4039(94)02404-Y
21. A.L. Chaffee and I. Liepa, "Microreactor for postcolumn reaction gas chromatography/mass spectrometry with fused silica capillary columns", Anal. Chem. 57, 2429 (1985). doi: 10.1021/ac00289a067
22. NIST/EPA/NIH Mass Spectral Library, v. 2.0. National Institute of Standards and Technology, Gaithersburg, MD, USA (2005).
23. R.M. Teeter, C.F. Spencer, J.W. Green and L.H. Smithson, "Analysis of alpha olefins using a gas chromatograph-mass spectrometer combination" J. Am. Oil Chem. Soc. 43, 82 (1966).
24. P. Issenberg P.A. Kobayashi and T.J. Mysliwy, "Combined gas chromatography-mass spectrometry in flavor research methods and applications", J. Agric. Food Chem. 17, 1377 (1969). doi: 10.1021/jf60166a014
25. A.I. Mikaya, V.I. Smetanin and V.G. Zaikin, "Reaction gas chromatography/mass spectrometry. 1. The system gas chromatograph-hydrogenation microreactor-mass spectrometer for the investigation of olefins", Izv. Akad. Nauk SSSR, Ser. Khim.(Russian) 2270 (1982).
26. A.I. Mikaya, L.P. Medvedkova, V.G. Zaikin, V.M. Vdovin and A.A. Kamishova, "Reaction gas chromatography/mass spectrometry for the investigation of cyclopropane-containing compounds" Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 1181 (1983).
27. V.G. Zaikin and A.I. Mikaya, "Mass spectrometry of bioorganic molecules containing small carbocycles", Mass Spectrom. Rev. 3, 479 (1984). doi: 10.1002/mas.1280030403
28. A.I. Mikaya, V.G. Zaikin and M.V. Tsodikov, "Reaction gas chromatography/mass spectrometry for the investigation of 1-aryl-2-(2-furyl) cyclopropanes", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 2494 (1986).
29. A.I. Mikaya, A.V. Antonova and V.G. Zaikin, "Gas phase oxidation in the inlet system of chromato-mass spectrometer for the investigation of alcohols", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 1436 (1982).
30. A.I. Mikaya, V.I. Smetanin, V.G. Zaikin, A.V. Antonova and N.S. Prostakov, "Reaction gas chromatography/mass spectrometry. 2. The use of catalytic on-line dehydrogenation for the investigation of alcohols by gas chromatography/mass spectrometry", Org. Mass Spectrom. 18, 99 (1983). doi: 10.1002/oms.1210180303
31. L.S. Glebov, A.I. Mikaya, A.E. Jatsenko, V.G. Zaikin, G.A. Kliger and S.M. Loktev, "Effective gas-phase deoxygenation of alcohols and ketones on iron catalyst", Tetrahedron Lett. 28, 3373 (1985). doi: 10.1016/S0040-4039(00)98301-1
32. L.S. Glebov, A.I. Mikaya, V.I. Smetanin, V.G. Zaikin, G.A. Kliger and S.M. Loktev, "Mechanism of gas-phase hydrogenation of alicyclic ketones on iron catalyst: effective experimental method on the basis of reaction gas chromatography/mass spectrometry", J. Catal. 93, 75 (1985). doi: 10.1016/0021-9517(85)90152-6
33. P. Wessels, J. Ogorka and G. Schwinger, "Elucidation of the structure of drug degradation products by online coupled reversed phase HPLC-GC-MS and online derivatization", J. High Res. Chromatogr. Chromatogr. Commun. 16, 708 (1993). doi: 10.1002/jhrc.1240161207
34. C.G. Chappell, C.S. Greaser and M.J. Shepherd, "On-line derivatization in combined high-performance liquid chromatography-gas chromatography-mass spectrometry", Analyst 122, 955 (1997). doi: 10.1039/a702003a
35. Th.P. Wampler, Applied Pyrolysis Handbook. Marcel Dekker Inc, New York, USA (1995).
36. L.E. Gusel'nikov, V.M. Sokolova, E.A. Volnina, V.G. Zaikin, N.S. Nametkin, M.G. Voronkov, S.V. Kirpichenko and V.V. Keiko, "Thermal isomerization and decomposition of 3,3-diethyl-2,4-dimethyl-3- silathietane", J. Organomet. Chem. 214, 145 (1981). doi: 10.1016/S0022-328X(00)86625-5
37. V.G. Zaikin, R.G. Mardanov and N.A. Plate, "Investigation of polymer microstructure by pyrolysis-gas chromatography/mass spectrometry", Visokomolek. Soedin. (Russian) 35, 1561 (1993).
38. 15N analysis with an extended dynamic range", Rapid Commun. Mass Spectrom. 13, 1237 (1999). doi: 10.1002/(SICI)1097-0231(19990715)13: 13<1237::AID-RCM633>3.0.CO;2-C
39. G.G. Esposito, "On-column formation and analysis of trimethylsilyl derivatives", Anal. Chem. 40, 1902 (1968). doi: 10.1021/ac60268a046
40. A.I. Mikaya, A.V. Ivanov and V.G. Zaikin, "The investigation of higher alcohols (in the form of silyl ethers) by gas chromatography/mass spectrometry", Petrochemistry (Russian) 28, 715 (1988).
41. A.I. Mikaya, A.V. Antonova, V.G. Zaikin, N.S. Prostakov, V.Ju. Rumjantsev, E.V. Slivinsky and S.M. Loktev, "Investigation of acyclic diols by gas chromatography/mass spectrometry with the use of on-column silylation", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 2502 (1983).
42. A.I. Mikaya, A.V. Antonova, V.G. Zaikin, N.S. Prostakov, V.Ju. Rumjantsev, E.V. Slivinsky and S.M. Loktev, "Gas chromatographic/mass spectrometric investigation of acyclic alkoxyalkanols as silyl ethers", J. General Chem. (Russian) 54, 653 (1984).
43. E.L. Nimz and S.L. Morgan, "On-line derivatization for complex fatty acid mixtures by capillary gas chromatography/mass spectrometry", J. Chromatogr. Sci. 31, 145 (1993).
44. M.W. Anders and G.J. Mannering, "New peak-shift technique for gas-liquid chromatography. Preparation of derivatives on the column", Anal. Chem. 34, 730 (1962). doi: 10.1021/ac60187a005
45. A.I. Mikaya, A.V. Ivanov and V.G. Zaikin, "Reaction gas chromatography/mass spectrometry. 15. The use of on-column acylation in a gas chromatograph/mass spectrometer for the investigation of amines within mixtures", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 2015 (1988).
46. D.R. Knapp, Handbook of Analytical Derivatization Reactions. John Wiley Inc., New York, USA (1979).
47. A.V. Ivanov, A.I. Mikaya and V.G. Zaikin, "Esterification of carboxylic acids in the inlet system of a gas chromatograph/mass spectrometer", Petrochemistry (Russian) 27, 262 (1987).
48. A.E. Jatsenko, A.I. Mikaya and V.G. Zaikin, "The use of on-column silylation of carbonyl compounds in a gas chromatograph/mass spectrometer", Izv. Akad. Nauk SSSR, Ser. Khim. 724 (1986).
49. P. Rudewicz and B. Munson, "Neutral reactions in gas chromatography/chemical ionization mass spectrometry", Anal. Chem. 57, 786 (1985). doi: 10.1021/ac00281a004
50. A.S. Christophersen, E. Hovland and J. Rasmunssen, "Glass capillary column gas chromatography of phenolalkylamines after flash-heater derivatization using a double injection technique", J. Chromatogr. 234, 107 (1982). doi: 10.1016/S0021-9673(00)81785-9
51. J. Lee, D. Lho, M. Kim, K. Kim and Y. Kim, "The effect of organic solvents on the determination of cyclic boronates of some β-blockers by gas chromatography/mass spectrometry", Rapid Commun. Mass Spectrom. 12, 1150 (1998). doi: 10.1002/(SICI)1097-0231(19980915)12:17<1150:: AID-RCM282>3.0.CO;2-5
52. M. Senn, W.J. Richter and A.L. Burlingame, "Convenient deuterium labeling for mass spectrometry via exchange of enolizable hydrogen on a gas-liquid chromatography column", J. Am. Chem. Soc. 87, 680 (1965). doi: 10.1021/ja01081a069
53. A.I. Mikaya, V.O. Zaikin, A.V. Antonova and N.S. Prostakov, "The use of on-line H/D exchange for the investigation of alcohols and carbonyl compounds by reaction gas chromatography/mass spectrometry", Org. Mass Spectrom. 19, 521 (1984). doi: 10.1002/oms.1210191015
54. D.F. Hagen, L.C. Haddad and J.S. Marchevka, "Solution and gas phase deuterium derivatization reactions for gas chromatography/microwave emission detection", Spectrochim. Acta 42B, 253 (1984).
55. A.I. Mikaya, A.V. Antonova, V.G. Zaikin and N.S. Prostakov, "Reaction gas chromatography/mass spectrometry. 7. The use of deuterium exchange on the column of a gas chromatograph/mass spectrometer for the investigation of aliphatic alcohols and carbonyl compounds", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 827 (1985).
56. A.I. Mikaya, A.V. Antonova, V.G. Zaikin, N.S. Prostakov, N.S. Wulfson and I.V. Torgov, "Investigation of steroid alcohols by reaction gas chromatography/mass spectrometry", Dokl. Akad. Nauk SSSR (Russian) 279, 396 (1984).
57. A.I. Mikaya, G.D. Romanov and V.G. Zaikin, "Gas-phase deuterium exchange of fluorenes, furans and thiophenes in the inlet system of gas chromatograph/mass spectrometer", Izv. Akad. Nauk SSR, Ser. Khim. (Russian) 739 (1991).
58. H. Elias, "Labeling by exchange on chromatographic columns", Adv. Chromatogr. 7, 243 (1968).
59. M.E. Mahmoud, A.M. Molissa, D.A. Forsyth and P. Vouros, "Hydrogen-deuterium exchange in fused-silica capillary columns", J. Chromatogr. 549, 416 (1991). doi: 10.1016/S0021-9673(00)91453-5
60. A.I. Mikaya, V.G. Zaikin and V.M. Vdovin, "Gas-phase deuteration of olefins over Wilkinson's catalyst", J. Mol. Catal. 32, 353 (1985). doi: 10.1016/0304-5102(85)85088-4
61. V.G. Zaikin and A.I. Mikaya, "Reaction gas chromatography/mass spectrometry. 6. Use of deuterium as the carrier and reagent gas in reaction gas chromatography/mass spectrometry", J. Chromatogr. 301, 77 (1984). doi: 10.1016/S0021-9673(01)89180-9
62. D.G. Earnshow, F.G. Doolittle and A.W. Decora, "Some mass spectral and analytical aspects of deuterium labeling of straight chain hydrocarbons", Org. Mass Spectrom. 5, 801 (1971). doi: 10.1002/oms. 1210050706
63. A.I. Mikaya, G.D. Romanov, V.G. Zaikin and V.M. Vdovin, "The use of deuteration in the inlet system of a gas chromatograph/mass spectrometer for the investigation of the fragmentation mechanisms of cyclobutane hydrocarbons", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 2405 (1985).
64. A.I. Mikaya, V.G. Zaikin, N.V. Ushakov and V.M. Vdovin, "Selective on-line deuteration in gas chromatography/mass spectrometry for the investigation of dissociative ionization of silicon-containing compounds", J. Organomet. Chem. 284, 5 (1985). doi: 10.1016/0022-328X(85)80007-3
65. F. Rinderknecht and B.J. Wenger, "The use of platinum-iridium for connecting or interfacing capillary columns in gas chromatography", High Res. Chromatogr. Chromatogr. Commun. 2, 746 (1979). doi: 10.1002/jhrc.1240021210
66. P.M. Woolard and A.I. Mallet, "Lipoxygenase products. A novel gas chromatographic-mass spectrometric assay for monohydroxy fatty acids", J. Chromatogr. 306, 1 (1984).
67. A.I. Mikaya, L.P. Medvedkova, V.G. Zaikin, I.A. Musaev, E.Kh. Kurashova, P.I. Sanin and V.M. Vdovin, "Investigation of cycloalkanes by reaction gas chromatography/mass spectrometry", Petrochemistry (Russian) 24, 173 (1984).
68. A.I. Mikaya, E.A. Trusova, V.G. Zaikin, N.P. Volinsky, E.N. Karaulova and G.D. Gal'pern, "Reaction gas chromatography/mass spectrometry. 4. Structure elucidation of cyclic sulphides by gas chromatography/mass spectrometry with the use of on-line hydrodesulphurization", Org. Mass Spectrom. 19, 428 (1984).
69. A.I. Mikaya, E.A. Trusova, V.G. Zaikin, L.A. Zigelman, A.B. Urin and N.P. Volinsky, "Reaction gas chromatography/mass spectrometry. 9. Post-column hydrodesulfurization in capillary GC/MS as an aid in structure elucidation of cyclic sulfides within mixtures", J. High Res. Chromatogr. Chromatogr. Commun. 7, 625 (1984). doi: 10.1002/jhrc.1240071105
70. A.I. Mikaya and V.G. Zaikin, "The determination of alkyl location in the molecules of alkylthiophenes by reaction gas chromatography/mass spectrometry", Izv. Akad. Nauk SSSR, Ser. Khim. (Russian) 2134 (1987).
71. W.V. Ligon and H. Grade, "Techniques for postcolumn derivatization in gas chromatography/mass spectrometry", Anal. Chem. 63, 255 (1991). doi: 10.1021/ac00003a013
72. 13C using mass fragmentography", Biomed. Mass Spectrom. 3, 1 (1976). doi: 10.1002/bms.1200030102
73. D.E. Matthews and J.M. Hayes, "Isotope-ratio-monitoring gas chromatography-mass spectrometry", Anal. Chem. 50, 1465 (1978). doi: 10.1021/ac50033a022
74. D.L. Hachey, W.W. Wong, T.W. Boutton and P.D. Klein, "Isotope ratio measurements in nutrition and biomedical research", Mass Spectrom. Rev. 6, 289 (1987). doi: 10.1002/mas.1280060203
75. H.J. Tobias, K.J. Goodman, C.E. Blacken and J.T. Brenna, "High-precision D/H measurement from hydrogen gas and water by continuous-flow isotope ratio mass spectrometry", Anal. Chem. 67, 2486 (1995). doi: 10.1021/ac00110a025
76. S. Prevost, T. Nicol, F. Monteau, F. André and B. Le Bizec, "Gas chromatography/combustion/isotope ratio mass spectrometry to control the misuse in breeding animals: new derivatization method applied to testosterone metabolites and precursors in urine samples", Rapid Commun. Mass Spectrom. 15, 2509 (2001). doi: 10.1002/rcm.538
77. 15N enrichments of urea in plasma by gas chromatography-combustion isotope ratio mass spectrometry and gas chromatography-mass spectrometry using the 2-methoxypyrimidine derivative", J. Chromatogr. B 791 (2003).
78. K. Blau and J.M. Halket (Eds). Handbook of Derivatives for Chromatography. John Wiley & Sons Ltd, Chichester, UK (1993).
79. V. Spikmans, S.J. Lane, B. Leavens, A. Manz and N.W. Smith, "On-line on-chip post-column derivatization reactions for preionization of analytes and cluster analysis in gradient μ-liquid chromatography/electrospray mass spectrometry", Rapid Commun. Mass Spectrom. 16, 1377 (2002). doi: 10.1002/rcm.727
80. th Conference on Mass Spectrometry and Allied Topics (Orlando, Florida, USA), p. 899 (1998).