Institute of Organic Chemistry, Technische Universität Carolo Wilhelmina zu Braunschweig, Hagenring 30, 38106, Braunschweig, Germany.
Institute of Pharmaceutical Biology, Technische Universität Carolo Wilhelmina zu Braunschweig, Mendelssohnstrasse 1, 38106, Braunschweig, Germany.
Chembiochem. 2019 Sep 16;20(18):2341-2345. doi: 10.1002/cbic.201900148. Epub 2019 Apr 25.
The synthesis of the first example of a fluorescent glucosinolate (GSL)-BODIPY conjugate based on an azide-containing artificial GSL precursor (GSL-N ) 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 holds potential for application as a fluorescence labeling tool to investigate GSL-associated processes.
报道了首例基于含叠氮基人工硫代葡萄糖苷（GSL-N）前体的荧光硫代葡萄糖苷（GSL）-BODIPY 缀合物的合成。对人工硫代葡萄糖苷的生化评估表明，在黑芥子酶存在下，这些化合物被转化为相应的异硫氰酸酯。此外，在植物专一性蛋白存在下，黑芥子酶催化水解生成了预期的替代产物，即腈。从 GSL-N 通过点击化学轻松组装荧光 GSL-BODIPY 缀合物，为作为荧光标记工具来研究与硫代葡萄糖苷相关的过程提供了应用潜力。
