Investigation into the Photosensitized Oxidation of Indole Derivatives
Mentor:Jeremy McCallum, Associate Professor of Chemistry, Loyola Marymount University
It has recently been demonstrated that antibodies can produce hydrogen peroxide catalytically when irradiated with light at 310 nm. The catalytic activity spectrum of this process mirrors the absorption spectrum of tryptophan, demonstrating the important role the photooxidation of tryptophan plays in this reaction. Our project centers on studying the mechanism by which indole derivatives are photooxidized and identifying the key intermediates formed from this process. The indole derivatives, 2-tert-butyl-tryptophol, 2-tert-butyl-tryptamine, and N-acetyl-2-tert-butyl-tryptamine were successfully synthesized via the Fischer indole synthesis. The protected tryptamine derivative was subjected to photosensitized oxidation via singlet oxygen and key oxidative intermediates were identified. Hydrogen peroxide production studies are currently under investigation.