Synthesis and Application of L-phenylalanine-4′-azobenzene

Hello! My name is Marshall Padilla, and I am a chemistry major and sophomore here at the College. I will be working with Dr. Young in the Chemistry Department to develop an unnatural amino acid. Amino acids are the building blocks of proteins, which in turn, are the workhorses of the cell. There exists twenty natural amino acids; but recently, researchers have began synthesizing unnatural amino acids. My amino acid (let’s call it AzoPhe for short) has a very peculiar property: when AzoPhe comes into contact with a specific wavelength of light, part of the molecule actually shifts, a feature called photoisomerability. This feature is useful, because when AzoPhe is inserted into a protein, and a specific wave length of light is shined on it, the amino acid will deactivate the protein. AzoPhe could also be utilized to block ion channels, which are important proteins that regulate ion concentration. After creating this amino acid, I will (hopefully) insert it into a protein called GFP, which is a fluorescent protein. If I successfully insert the amino acid into specific locations (residues) of the protein, I will be able to activate and deactivate the protein’s ability to fluoresce via AzoPhe’s photoisomerability. The ability to control a protein offers a powerful medical tool, as the misregulation and misexpression of proteins is often the root of health conditions.

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