Synthesis of an Unnatural Fluorescent Amino Acid
Arts and Sciences
Moriah Carmel: orcid.org/0000-0002-7073-6246 Hannah Laatsch: orcid.org/0000-0002-0919-5102
The long-term goal of this project is to chemically synthesize an unnatural fluorescent amino acid (UFAA) that can later be used to build glow-in-the-dark proteins. UFAAs allow the visualization of a single protein in an otherwise transparent living cell. The specific objective of this project is to synthesize a 4-(N,N-dimethylamino)phthalimide-based environment-sensitive fluorescent amino acid. The first part of this synthesis was the preparation of an anhydride (4-Methyl-Aminophthalic Anhydride), which was then coupled with commercially-available Boc-Dap-OtBu Hydrochloride. Finally, trifluoroacetic acid was used to remove the protecting groups, yielding the desired product. The product was characterized using 1H and 13C NMR, and Liquid Chromatography-Mass Spectrometry (LC-MS). The remaining tasks include improving the purification and percent yield.
Laatsch, Hannah J.; Carmel, Moriah G.; and Goyne, Thomas, "Synthesis of an Unnatural Fluorescent Amino Acid" (2018). Summer Interdisciplinary Research Symposium. 41.