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Scholars Day 2006, Wednesday, April 12

The Synthesis of Amino-Substituted Alkylaryltelluride Phosphonium Salts

This presentation describes the successful synthesis and characterization of four electron-rich amino-substituted alkylaryltelluride phosphonium salts. These compounds will be evaluated as probes of oxidative damage and repair in yeast mitochondria. Alkylaryltellurides were chosen because they are known to act as antioxidants by readily losing an electron under oxidizing conditions and by oxidizing to the telluroxide in the presence of two-electron oxidants. More specifically, tellurides having amino-substituted aryl rings are most easily oxidized, thus making them better antioxidants. The presence of a triphenylphosphonium group at the terminus of the alkyl group of the alkylaryltellurides should result in improved transport into yeast mitochondria, as has been shown by others for lipophilic cationic derivatives of the antioxidant vitamin E (a one-electron antioxidant). The four amino-substituted alkylaryltelluride phosphonium salts were prepared in moderate yield in a three-step synthesis from the corresponding anilines. They were then purified by chromatography and recrystallization, and characterized by proton, carbon-13, and 2-dimensional NMR spectroscopy.

Presenter: Jacqueline Simson (Undergraduate Student)
Topic: Chemistry
Location: 101 Edwards
Time: 9:45 am (Session I)