Synthesis of an Unnatural Fluorescent Amino Acid

Primary Submission Contact

Thomas Goyne

Faculty Sponsor

Thomas Goyne

Faculty Sponsor Email Address



Arts and Sciences



Document Type

Poster Presentation


Fall 10-26-2018


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.

Biographical Information about Author(s)

Moriah Carmel is a Senior Chemistry Major. Hannah Laatsch is a Senior Chemistry Major. Dr. Thomas Goyne is an Associate Professor of Chemistry at Valparaiso University.

Additional Presentation Information

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