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New cysteine-modifying reagents: Efficiency of derivatization and influence on the signals of the protonated molecules of disulfide-containing peptides in matrix-assisted laser desorption/ionization mass spectrometry

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Abstract

Mass spectrometric de novo sequencing of skin secretion peptides from genus Rana is complicated because of C-terminal disulfide cycles present in their structure. Brevinin-1E and brevinin-2Ec from the skin secretion of the Marsh Frog R. ridibunda were used for a comparative study of six N-phenylmaleimide derivatives as new alkylating agents for cysteine thiol moieties. The paper describes the synthesis and confirmation of the structures of the obtained compounds. A procedure was developed for modifying thiol groups with the proposed reagents. Alkylation efficiency and the effect on the peak intensity in matrix-assisted laser desorption/ionization (MALDI) spectra were investigated. The best results were obtained for 2,4- and 2,5-dimethylphenylmaleimides. Additionally tested iodoacetic acid was shown to be a powerful modifier of thiol groups, while its excess notably increases the intensities of the peaks of protonated molecules in the MALDI mass spectra of both peptides.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Moscow, 119991, Russia

    T. Yu. Samgina, V. A. Gorshkov, E. A. Vorontsov, V. V. Bagrov, I. E. Nifant’ev & A. T. Lebedev

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  1. T. Yu. Samgina
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  2. V. A. Gorshkov
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  3. E. A. Vorontsov
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  4. V. V. Bagrov
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  5. I. E. Nifant’ev
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  6. A. T. Lebedev
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Corresponding author

Correspondence to A. T. Lebedev.

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Original Russian Text © T.Yu. Samgina, V.A. Gorshkov, E.A. Vorontsov, V.V. Bagrov, I.E. Nifant’ev, A. T. Lebede, 2010, published in Mass-spektrometria, 2010, 6(3), pp. 178–186.

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Samgina, T.Y., Gorshkov, V.A., Vorontsov, E.A. et al. New cysteine-modifying reagents: Efficiency of derivatization and influence on the signals of the protonated molecules of disulfide-containing peptides in matrix-assisted laser desorption/ionization mass spectrometry. J Anal Chem 65, 1320–1327 (2010). https://doi.org/10.1134/S1061934810130034

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  • DOI: https://doi.org/10.1134/S1061934810130034

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