A pitfall of using 2-[(2E)-3-(4-tert-butylphenyl)- 2-methylprop-2- enylidene]malononitrile as a matrix in MALDI TOF MS: Chemical adduction of matrix to analyte amino groups

Journal of Mass Spectrometry

Volumn 45, Issue 10, 2010, Pages 1195-1202

  Lou, Xianwen ^a   De Waal, Bas F M ^a   Van Dongen, Joost L J ^a   Vekemans, Jef A J M ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Amine; Analyte matrix reaction; DCTB; MALDI TOF MS; Matrix adduction

Indexed keywords

ALIPHATIC PRIMARY AMINES; AMINO GROUP; ANALYTES; AROMATIC AMINES; DCTB; DICYANOMETHYLENE; GASPHASE; ION PEAKS; MALDI TOF MS; MALONONITRILES; MASS DIFFERENCE; MATRIX; MATRIX ASSISTED LASER DESORPTION/IONIZATION; NUCLEOPHILIC REACTION; RADICAL CATIONS; SECONDARY AMINES; SECONDARY AMINO GROUP; SYNTHETIC COMPOUNDS; TERTIARY AMINE; TIME OF FLIGHT MASS SPECTROMETRY;

AMINES; AROMATIC COMPOUNDS; CHEMICAL ANALYSIS; DESORPTION; MASS SPECTROMETRY;

AMINATION;

2 [3 (4 TERT BUTYLPHENYL) 2 METHYLPROP 2 ENYLIDENE]MALONONITRILE; ALIPHATIC AMINE; AROMATIC AMINE; CATION; MALONONITRILE; RADICAL; TERTIARY AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; GAS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON TRANSPORT;

AMINES; CHEMICAL PROCESSES; DENDRIMERS; NITRILES; POLYETHYLENE GLYCOLS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 78650838935     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1814     Document Type: Article

References (26)

1. L. Ulmer, J. Mattay, H. G. Torres-Garcia, H. Luftmann. The use of 2-[(2E)-3-(4-tert-butylphenyl)-2-methylprop-2- enylidene)dicyanomethylene group as matrix for matrix assisted laser desorption/ionization mass spectrometry. Eur. J.Mass Spectrom. 2000, 6, 49.
2. T. Brown, N. L. Clipston, N. Simjee, H. Luftmann, H. Hungerbühler, T. Drewello. Matrix-assisted laser desorption/ionization of amphiphilic fullerene derivatives. Int. J. Mass Spectrom. 2001, 210, 249.
3. D. Fati, V. Leeman, Y. V. Vasil'ev, T. Drewello, B. Leyh, H. Hungerbühler. Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization. J.Am. Soc. Mass Spectrom. 2002, 13, 1448.
4. D. Fati, Y. V. Vasil'ev, N. K.Wachter, R. Taylor, T. Drewello. MALDI mass spectrometric determination of molecular site-specific charge localization, and laser induced coalescence reactivity of fullerenodendrimers. Int. J. Mass Spectrom. 2003, 229, 3.
5. l6. Chem. Eur. J. 2005, 11, 5426.
6. A. V. Streletskii, I. N. Ioffe, S. G. Kotsiris, M. P. Barrow, T. Drewello, S. H. Strauss, O. V. Boltalina. In-plume thermodynamics of the MALDI generation of fluorofullerene anions. J. Phys. Chem. A. 2005, 109, 714.
7. Y. V. Vasil'ev, O. G. Khvostenko, A. V. Streletskii, O. V. Boltalina, S. G. Kotsiris, T. Drewello. Electron transfer reactivity in matrixassisted laser desorption/ionization (MALDI): Ionization energy, electron affinity and performance of the DCTB matrix within the thermochemical framework. J. Phys. Chem. A. 2006, 110, 5967.
8. M. F.Wyatt, B. K. Stein, A. G. Brenton. Characterization of various analytes using matrix-assisted laser desorption/ionization timeof- flight mass spectrometry and 2-[(2E)-3-(4-tert-butylphenyl)-2- methylprop-2-enylidene] dicyanomethylene group matrix. Anal. Chem. 2006, 78, 199.
9. L.Xue, U. S.Agarwal, M. B. B. P. Staal, A.H. E.Müller, C. M. E. Bailly, P. J. Lemstra. Synthesis and direct topology visualization of highmolecular- weight star PMMA. Macromolecules 2005, 38, 2093.
10. A. Müller, E. Diemann, S. Q. N. Shah, C. Kuhlmann, M. C. Letzel. Soccer-playing metal oxide giant spheres: A first step towards patterning structurally well defined nano-object collectives. Chem. Commun. 2002, 440.
11. M. A. R. Meier, U. S. Schubert. Integration of MALDI-TOFMS as highthroughput screening tool into the workflow of combinatorial polymer research. Rev. Sci. Instrum. 2005, 76, 062211.
12. S.Huijser, B. B. P. Staal, J. Huang, R. Duchateau, C. E. Koning. Chemical composition and topology of poly(lactide-co-glycolide) revealed by pushing MALDI-TOF MS to its limit. Angew. Chem. Int. Ed. 2006, 45, 4104.
13. X. Lou, J. van Buijtenen, J. J. A. M. Bastiaansen, B. F. M. de Waal, B. M.W. Langeveld, J. L. J. van Dongen. Characterization of some synthetic Ru and Ir complexes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. J. Mass Spectrom. 2005, 40, 654.
14. 3-symmetric disks and their precursors by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. J.Mass Spectrom. 2006, 41, 659.
15. x. J. Am. Chem. Soc. 2008, 130, 5940.
16. R. C. Beavis, B. T. Chait. Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins. Rapid Commun.Mass Spectrom. 1989, 3, 432.
17. R. C. Beavis, B. T. Chait. High-accuracy molecular mass determination of proteins using matrix-assisted laser desorption mass spectrometry. Anal. Chem. 1990, 62, 1836.
18. A. V. Loboda, A. N. Krutchinsky,M. Bromirski,W. Ens, K. G. Standing. A tandem quadrupole/time-of-flight mass spectrometer with a matrix-assisted laser desorption/ionization source: Design and performance. Rapid Comun.Mass Spectrom. 2000, 14, 1047.
19. A. V. Loboda, I. V. Chernushevich. Investigation of the mechanism of matrix adduct formation in MALDI at elevated pressure. Int. J. Mass Spectrom. 2005, 240, 101.
20. E. M. M. de Brabander-van den Berg, E. W. Meijer. Poly(propylene imine) dendrimers: Large scale synthesis by heterogeneously catalyzed hydrogenations. Angew. Chem. Int. Ed. Eng. 1993, 32, 1308.
21. A. W. Bosman, H. M. Janssen, E. W. Meijer. About dendrimers: Structure, physical properties and applications. Chem. Rev. 1999, 99, 1665.
22. J. W. Weener, J. L. J. van Dongen, E. W. Meijer. Electrospray mass spectrometry of poly(propylene imine) dendrimers-probing the reactivity in the gas phase. J. Am. Chem. Soc. 1999, 121, 10346.
23. J. C. M. van Hest, D. A. P. Delnoye, M. W. P. L. Baars, M. H. P. van Genderen, E. W. Meijer. Polystyrene-dendrimer amphiphilic block copolymers with a generation dependant aggregation. Science 1995, 268, 1592.
24. S. Langereis, Q. G. de Lussanet, M. H. P. van Genderen,W. H. Backes, E. W. Meijer. Multivalent contrast agents based on Gd(III)DTPAterminated poly(propylene imine) dendrimers for magnetic resonance imaging. Macromolecules 2004, 37, 3084.
25. M. A. C. Broeren, B. F. M. de Waal, M. H. P. van Genderen, H. M. H. F. Sanders, G. Fytas, E. W. Meijer. Muticomponent host-guest chemistry of carboxylic acid and phosphonic acid based guests with dendritic hosts: An NMR study. J. Am. Chem. Soc. 2005, 127, 10334.
26. M. Karas, M. Gluckmann, J. Schafer. Ionization in matrix-assisted laser desorption/ionization: Singly charged molecule ions are the lucky survivors. J.Mass Spectrom. 2000, 35, 1.