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The Tandem Mannich–Electrophilic Amination Reaction: a Versatile Platform for Fluorescent Probing and Labeling

Authors

  • Dr. Jarosław Sączewski,

    Corresponding author
    1. Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk (Poland), Fax: (+48) 583493257
    • Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk (Poland), Fax: (+48) 583493257
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  • Dr. Krzysztof Hinc,

    1. Intercollegiate Faculty of Biotechnology UG & MUG, Medical University of Gdansk, Ul. Dębinki 1, 80-211 Gdańsk (Poland)
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  • Dr. Michał Obuchowski,

    1. Intercollegiate Faculty of Biotechnology UG & MUG, Medical University of Gdansk, Ul. Dębinki 1, 80-211 Gdańsk (Poland)
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  • Prof. Maria Gdaniec

    1. Faculty of Chemistry, Adam Mickiewicz University, Ul. Grunwaldzka 6, 60-780 Poznań (Poland)
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Abstract

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Tandem fluorogenic reaction: A new platform for the direct, selective and sensitive detection of formaldehyde and/or secondary aliphatic amines, based on a tandem Mannich–electrophilic amination reaction, is described. Biological applications of hydrophilic, water-soluble fluorescent 2,2-dialkyl-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-2-ium-8-carboxylates (Safarinium P probes) are exemplified by labeling of the amine-containing Ac-AKF-NH2 peptide and Bacillus subtilis spores in aqueous solution.

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Article Information

DOI

10.1002/chem.201302085

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Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • amination;
  • dyes/pigments;
  • fluorogenic reaction;
  • mannich bases;
  • tandem reaction

Publication History

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  • Manuscript Received:

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Citing Literature

  • Number of times cited: 1
  1. 1Jarosław Sączewski, Joanna Fedorowicz, Martyna Korcz, Franciszek Sączewski, Barbara Wicher, Maria Gdaniec, Agnieszka Konopacka, Experimental and theoretical studies on the tautomerism and reactivity of isoxazolo[3,4-b]quinolin-3(1H)-ones, Tetrahedron, 2015, 71, 47, 8975CrossRef