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Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)
Author(s) -
Glindemann Carina Patrizia,
Backenköhler Anita,
Strieker Matthias,
Wittstock Ute,
Klahn Philipp
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201900148
Subject(s) - myrosinase , glucosinolate , conjugate , chemistry , fluorescence , click chemistry , azide , hydrolysis , bodipy , combinatorial chemistry , biochemistry , organic chemistry , biology , botany , brassica , mathematical analysis , physics , mathematics , quantum mechanics
The synthesis of the first example of a fluorescent glucosinolate (GSL)–BODIPY conjugate based on an azide‐containing artificial GSL precursor (GSL‐N 3 ) 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‐N 3 holds potential for application as a fluorescence labeling tool to investigate GSL‐associated processes.