Diets rich in <i>Brassica</i> vegetables provide a variety of anticancer benefits, largely due to the presence of glucosinolates, β-thioglucoside-<i>N</i>-hydroxysulfates, which are abundant in the plants. The action of the enzyme myrosinase on glucosinolates evolves biologically-active isothiocyanates (ITCs), cellular electrophiles which are believed to be partially responsible for the anti-cancer properties of these vegetables. The non-natural ITCs 4-(methylsulfinyl)benzyl ITC and 3-pyridylmethyl ITC have been shown to be potent inducers of antioxidant response element (ARE) promoted genes. Since myrosinase is known to be tolerant of non-natural glucosinolate substrates, this study describes efforts to utilize the nitronate synthetic pathway toward the preparation of four non-natural glucosinolate precursors related to these target ITCs: 4-(methylthio)benzyl glucosinolate, 4-(methylsulfinyl)benzyl glucosinolate, 4-(methylsulfonyl)benzyl glucosinolate, and 3-pyridylmethyl glucosinolate.

Synthesis of glucosinolates via the nitronate pathway

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.