Thiosemicarbazones (TSCs) are a class of compounds with known antibacterial, antifungal, and antiviral properties. Some are known inhibitors of the enzyme tyrosinase, which is responsible for browning in fruits and vegetables. Our research group recently developed a greener synthesis for TSCs. Compared to traditional methods, reactions with our greener method require less energy, are faster, and still result in good to excellent purities and yields without recrystallization. A total of 18 TSCs have been made thus far. Students successfully made all of the TSCs and tested them on a variety of fruits and vegetables for tyrosinase inhibition. The assay used allowed for a quick and easy qualitative analysis of inhibitory activity against tyrosinase in an organic laboratory setting. Collaboration with biochemistry students allowed our organic students to pass on promising TSCs for quantitative analysis in the biochemistry laboratory. This project has been tested several times each in both one-semester and two-semester organic courses and twice in a first-semester biochemistry course.

Greener synthesis of thiosemicarbazones and a qualitative tyrosinase inhibition assay for organic chemistry laboratory

251st National Meeting (2016)

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