chemistry major, basic organic chemistry skills in theory and practice
N-acyl-7-nitroindolines are photoreactive compounds that are capable of an acyl transfer to a variety of nucleophiles, such as amines, aminals, hydrazine, alcohols, and thiols (see three publications from our research group: Kaneshiro & Michael, Angew. Chem. Int. Ed. 2006, 45, 1077; Hogenauer et al., Org. Biomol. Chem. 2007, 5, 759; and Pardo et al., ChemBioChem 2015, 16, 1884). These photochemical acylation reactions produce amides, oxoesters, thioesters, and hydrazides under mild, neutral conditions, and are therefore very useful synthetic tool. The photochemical reaction is typically carried out in inert organic solvents. In water, a different photolysis mechanism leading to carboxylic acids has been discovered (Morrison et al., Photochem. Photobiol. Sci. 2002, 1, 960). It would be a breakthrough in the field of synthetic photochemistry if the acyl transfer photochemistry could tolerate a wide variety of solvents including aprotic and protic solvents, because it would open doors to the mild, photochemical synthesis of a number of sensitive biomolecules that are only soluble in polar solvents such as water and alcohols. We believe that the installation of two methyl groups at position 2 of the nitroindoline ring changes its photochemical properties and will result in a superior photoreactive compound that tolerates a wide variety of solvents.
The undergraduate student will receive training in the laboratory techniques required for the synthesis of small heterocyclic molecules, in synthetic photochemistry, in compound purification by chromatography, and in compound analysis by mass spectrometry, and 1H and 13C nuclear magnetic resonance spectroscopy.