Abstract
Tetrahydrofuran (THF) is one of the most frequently used solvents in the MALDI TOF MS analysis of synthetic compounds. However, it should be used with caution because a trace amount of 4-hydroxybutanal (HBA) might be generated and accumulated in THF during storage. Since only a tiny amount of analytes is required in MALDI MS measurements, a trace amount of HBA might have a significant effect on the MS results. It was found that HBA will quickly react with primary and secondary amino compounds, leading to false results about the sample composition with an extra series of ions with additional mass of 70 Da in between. The formation of HBA can be inhibited by butylated hydroxytoluene (BHT) antioxidant. Therefore, when THF is required as the solvent for sample preparation, it is strongly recommended to use a BHT-stabilized one, at least for the analysis of compounds with amino groups.
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References
Yalcin, T., Dai, Y., Li, L.: Matrix assisted laser desorption ionization mass spectrometry for polymer analysis: solvent effects in sample preparation. J. Am. Soc. Mass Spectrom. 9, 1303–1310 (1998)
Figueroa, I.D., Torres, O., Russell, D.H.: Effects of water in the sample preparation for MALDI on the mass spectra. Anal. Chem. 70, 4527–4533 (1998)
Cohen, S.L., Chait, B.T.: Influence of matrix solution conditions on the MALDI-MS analysis of peptides and proteins. Anal. Chem. 68, 31–37 (1996)
Kussmann, M., Nordhoff, E., Rahbek-Nielsen, H., Haebel, S., Rossel-Larsen, M., Jakobsen, L., Gobom, J., Mirgorodskaya, E., Kroll-Kristensen, A., Palm, L., Roepstorff, P.: Matrix-assisted laser desorption/ionization mass spectrometry sample preparation techniques designed for various peptide and protein analytes. J. Mass Spectrom. 32, 593–601 (1997)
Criegee, R.: Über das tetrahydrofuran-peroxyd. Angew. Chem. 62, 120 (1950)
Carey, F.A.: Organic chemistry, 7th edn. McGraw Hill Higher Education, New York (2008)
Zagorevskii, D.M., Nasrullah, M.J., Raghunadh, V., Benicewicz, C.: The effect of tetrahydofuran as solvent on matrix-assisted laser desorption ionization and electrospray ionization mass spectra of functional polystyrenes. Rapid Commun. Mass Spectrum. 20, 178–180 (2006)
Albertazzi, L., Martinez-Veracoechea, F.J., Leenders, C.M.A., Voets, I.K., Frenkel, D., Meijer, E.W.: Spatiotemporal control and superselectivity in supermolecular polymers using multivalency. Proc. Natl. Acad. Sci. U. S. A. 110, 12203–12204 (2013)
Kaeser, A., Schenning, A.P.H.J.: Fluorescent nanoparticles based on self-assembled π-conjugated systems. Adv. Mater. 22, 2985–2997 (2010)
de Brabander-van den Berg, E.M.W., Meijer, E.W.: Poly(propylene imine) dendrimers: large scale synthesis by heterogeneously catalyzed hydrogenations. Angew. Chem. Int. Ed. Eng. 32, 1308–1311 (1993)
Leenders, C.M.A., Albertazzi, L., Mes, T., Koenigs, M.M.E., Palmans, A.R.A., Meijer, E.W.: Superamolecular polymerization in water harnessing both hydrophobic effects and hydrogen bond formation. Chem. Commun. 49, 1963–1965 (2013)
Petkau, K., Kaeser, A., Fischer, I., Brunsveld, L., Schenning, A.P.H.J.: Pre- and post-functionalized self-assembled π-conjugated fluorescent organic nanoparticles for dual targeting. J. Am. Chem. Soc. 133, 17063–17071 (2011)
Bosman, A.W., Janssen, H.M., Meijer, E.W.: About dendrimers: structure, physical properties and applications. Chem. Rev. 99, 1665–1688 (1999)
Lou, X., van den Hout, K.P., van Houtem, M.H.C.J., van Dongen, J.L.J., Vekemans, J.A.J.M., Meijer, E.W.: Radical cation formation in characterization of novel C3-symmetric disks and their precursors by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. J. Mass Spectrom. 41, 659–669 (2006)
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Lou, X., Leenders, C.M.A., van Onzen, A.H.A.M. et al. False Results Caused by Solvent Impurity in Tetrahydrofuran for MALDI TOF MS Analysis of Amines. J. Am. Soc. Mass Spectrom. 25, 297–300 (2014). https://doi.org/10.1007/s13361-013-0766-y
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DOI: https://doi.org/10.1007/s13361-013-0766-y