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Abstract
Glucosinolates (GSLs) are secondary metabolites produced as part of an herbivore defence system in plants of the order Brassicales. GSLs release isothiocyanates (ITCs) upon activation by the myrosinase. Beyond their herbivore feeding deterrent properties, these ITCs have multiple interesting bioactivities. However, their release is limited by the presence of myrosinase. Here, we report the concept of pseudoglucosinolates (psGSLs) hijacking the natural release mechanism of GSLs for the release of ITCs and adapting it to nitroreductase as the triggering enzymes. We provide proof-of-concept for nitroreductase-responsive psGSLs and demonstrate their potential for peptide labelling, ITC-prodrug approaches and for in vivo applications using the nematode of C. elegans.
Supplementary materials
Title
Supporting Information
Description
Description of general experimental procedure, synthesis of the compounds, biochemical evaluation and data of compound characterization.
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Supplementary weblinks
Title
Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases
Description
Primary NMR data of the compounds.
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Proteomic data
Description
Mass spectrometric data for all proteomic analyses have been deposited to the ProteomeXchange Consortium (http://proteomecentral.proteomexchange.org) via the PRIDE partner repository with the dataset identifier PXD049355 and will be publicly available after final publication of the manuscript.
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