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1-Pyrenylboronic Acid as a Reactive Matrix for the Analysis of Polyfunctional Compounds by MALDI Mass Spectrometry: New Possibilities

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Abstract

1-Pyrenylboronic acid (1-PBA) is a type of a reactive matrix useful for the analysis of polyfunctional compounds by MALDI mass spectrometry. It exhibits conventional matrix properties (absorption and transfer of laser radiation energy) and acts as a derivatizing reagent capable of interacting with vicinal functional groups under mild conditions and forming covalent adducts. Pyrenyl group in its structure, which has high ability to absorb UV laser quanta, ensures the detection of analyte derivatives containing a 1-PBA residue as radical cations, which is untypical for MALDI. The effectiveness of its use was earlier proved for compounds containing 1,2-diol fragments. This work presents additional cases of using this reactive matrix in the analysis of practically significant compounds of this type, demonstrating that 1-PBA can also react with distant OH groups. Many examples show its applicability to the study of various α-hydroxy acids and vicinal aminols and capability of forming cyclic covalent adducts with 1,2-diamines.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Collective Use Center “Analytical Center for Problems of Deep Processing of Oil and Petrochemistry” of the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Funding

The study was supported by the Russian Foundation for Basic Research and the Government of Moscow as part of scientific projects nos. 21-33-70059 (study of using 1-PBA to detect diols) and 19-33-60037 (study of using 1-PBA to detect carboxylic acids).

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Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    M. D. Matveeva, M. E. Zimens, A. P. Topolyan, D. I. Zhilyaev, D. L. Voskressenskaya, M. S. Krivosheina, R. S. Borisov & V. G. Zaikin

  2. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    A. P. Topolyan

  3. Peoples’ Friendship University of Russia (RUDN University), 117198, Moscow, Russia

    D. I. Zhilyaev, D. L. Voskressenskaya & R. S. Borisov

Authors
  1. M. D. Matveeva
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  2. M. E. Zimens
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  3. A. P. Topolyan
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  4. D. I. Zhilyaev
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  5. D. L. Voskressenskaya
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  6. M. S. Krivosheina
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  7. R. S. Borisov
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  8. V. G. Zaikin
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All authors equally contributed to this work.

Corresponding author

Correspondence to R. S. Borisov.

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The authors declare that they have no conflicts of interest.

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Translated by O. Zhukova

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Matveeva, M.D., Zimens, M.E., Topolyan, A.P. et al. 1-Pyrenylboronic Acid as a Reactive Matrix for the Analysis of Polyfunctional Compounds by MALDI Mass Spectrometry: New Possibilities. J Anal Chem 77, 1729–1736 (2022). https://doi.org/10.1134/S1061934822140040

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  • DOI: https://doi.org/10.1134/S1061934822140040

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