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Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass
Antoine Lizzul-Jurse1, Laetitia Bailly1, Marie Hubert-Roux1
1Normandie Univ, COBRA, UMR 6014 & FR 3038, Univ Rouen-Normandie, INSA Rouen, CNRS, 1 rue Tesnière 76821 Mont-Saint-Aignan, Cedex, France. cyrille.sabot@univ-rouen.fr.
Abstract:
Fluorescent coumarins are an important class of small-molecule organic fluorophores ubiquitous in different well-established and emerging fields of research including, among others, biochemistry and chemical biology. The present work aims at covering the poor detectability of coumarin-based conjugates by mass spectrometry while keeping important photophysical properties of the coumarin core. In this context, the synthesis of readily functionalizable phosphonium-tagged coumarin derivatives enabling a dual mass-tag and fluorescence labelling of analytes or (bio)molecules of interest through a single-step protocol, is reported. The utility of these coumarins is illustrated through the preparation of fluorogenic substrates that facilitated identification of the peptide fragment released by specific proteolytic cleavages.
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