Glaser-Hay Conjugation Results

After 7 weeks of research I had finally reached a point where I would be able to conduct experiments on the green fluorescent protein I had synthesized and collect results! I began working with the p-propargyloxyphenylalanine (pPrF) GFP as I had synthesized that successfully first. The unnatural amino acid pPrf is synthesized using the starting material tyrosine and propargyl bromide. Once the two are reacted, the hydrogen on the tyrosine side group oxygen is pushed off and the oxygen is now bonded to a propargyl group. The propargyl group, which contains a C-C triple bond, introduces a functionality which is not naturally present in amino acids and proteins. This allows us to conduct alkyne reactions with specificity. In order to understand the properties of the fluorophore, I set up an experiment where the UAA would be reacted with alkyne molecules. This unique reaction is known as the Glaser-Hay Reaction and allows us to create artificial polyynes. After the Glaser-Hay reactions were conducted with various alkyne molecules, emission spectra were collected for each of the reactions. We were able to see significant shifts in fluorescence peaks with the various molecules which meant that the weeks of work had paid off with some very interesting results!

Thanks for reading!