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Diverted Natural Lossen-type Rearrangement for Bioconjugation through in Situ Myrosinase-Triggered Isothiocyanate Synthesis

Abstract : Fluorescein isothiocyanate (FITC) is one of the most extensively used fluorescent probes for the labeling of biomolecules. The isothiocyanate function reacts with lysine residues of proteins to provide a chemically stable thiourea linkage without releasing any byproduct. However, diversification of isothiocyanate-based reagents is still hampered by the lack of mild conditions to generate isothiocyanate chemical functions, as well as by their poor stability and limited solutions available to increase water solubility, restricting the use of isothiocyanate labeling to highly water-soluble fluorophores. Inspired by plant biological processes, we report a safe and biocompatible myrosinase-assisted in situ formation of isothiocyanate conjugates from a highly water-soluble and stable glucosinolate precursor. This method was applied for the fluorescence labeling of a plasmatic protein and fluorescence imaging of living cells.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02280045
Contributor : Hélène Castel <>
Submitted on : Thursday, September 5, 2019 - 7:20:04 PM
Last modification on : Thursday, July 30, 2020 - 3:06:26 AM

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Jean Wilfried Fredy, Giuliano Cutolo, Benjamin Poret, Reine Nehmé, Marie Hubert-Roux, et al.. Diverted Natural Lossen-type Rearrangement for Bioconjugation through in Situ Myrosinase-Triggered Isothiocyanate Synthesis. Bioconjugate Chemistry, American Chemical Society, 2019, 30 (5), pp.1385-1394. ⟨10.1021/acs.bioconjchem.9b00153⟩. ⟨hal-02280045⟩

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