Light-directed derivatization, caging, and releasing methodologies based on o-quinone methide chemistry

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With this award, the Chemical Synthesis Program of the Chemistry Division is funding Professor Vladimir Popik of the Department of Chemistry at the University of Georgia to design and synthesize novel UV and NIR-sensitive photolabile protecting groups and photocleavable linkers, as well as develop methods for the selective photo-derivatization and release of thiol moieties in various substrates. Photolabile protecting groups allow for the spatiotemporal control of substrate activation, as well as for 'reagentless' deprotection. Release of active compounds using light at the red edge of the visible spectrum extends the utility of the 'caging' technique in biology as it minimizes photo-damage to cells and might be useful for experiments in mammalian tissues.. This project aims to provide organic, biological, and medicinal chemists with new tools to control activity of caged compounds in time and in space, with potentially broad application. For example, the selective and reversible derivatization of native or genetically engineered cysteine residues in proteins may allow for the remote control of their activity. Reversible immobilization can be useful for modification or repair of sensor arrays. This project will provide undergraduate and graduate students, including those from groups historically underrepresented in the sciences, with interdisciplinary training at the interface of synthetic and physical organic chemistry, with elements of photochemistry, biochemistry, and material science.