Bioresponsive pseudoGlucosinolates (psGSLs) release Isothiocyanates (ITCs) in the Presence of Nitroreductases

21 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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 triggering enzymes. We provide the proof-of-concept for nitroreductase-responsive psGSLs and demonstrate their potential for peptide labelling and ITC-prodrug approaches.


artificial glucosinolates
bioresponsive protein labeling

Supplementary materials

Supporting Information
Description of general experimental procedure, synthesis of the compounds, biochemical evaluation and data of compound characterization.

Supplementary weblinks


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