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Issue 32, 2016
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Readily functionalizable phosphonium-tagged fluorescent coumarins for enhanced detection of conjugates by mass spectrometry

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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.

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

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Supplementary files

Article information


Submitted
17 May 2016
Accepted
20 Jul 2016
First published
21 Jul 2016

Org. Biomol. Chem., 2016,14, 7777-7791
Article type
Paper

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

A. Lizzul-Jurse, L. Bailly, M. Hubert-Roux, C. Afonso, P. Renard and C. Sabot, Org. Biomol. Chem., 2016, 14, 7777
DOI: 10.1039/C6OB01080F

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