Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

Abstract

The synthesis of the first example of a fluorescent glucosinolate (GSL)-BODIPY conjugate based on an azide-containing artificial GSL precursor (GSL-N₃ ) is reported. Biochemical evaluation of the artificial GSLs revealed that the compounds are converted to the corresponding isothiocyanates in the presence of myrosinase. Furthermore, myrosinase-catalyzed hydrolysis in the presence of plant specifier proteins yielded the expected alternative products, namely nitriles. The easy assembly of the fluorescent GSL-BODIPY conjugate by click chemistry from GSL-N₃ holds potential for application as a fluorescence labeling tool to investigate GSL-associated processes.

Keywords: artificial natural product derivatives; fluorescence labeling; glucosinolates; isothiocyanates; thioglucosidases.