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Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass spectrometry

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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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046223
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:58 PM
Last modification on : Thursday, July 2, 2020 - 3:29:06 AM

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Antoine Lizzul-Jurse, Laëtitia Bailly, Marie Hubert-Roux, Carlos Afonso, Pierre-Yves Renard, et al.. Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass spectrometry. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2016, 14 (32), pp.7777-7791. ⟨10.1039/c6ob01080f⟩. ⟨hal-02046223⟩

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