Synthesis of an Unnatural Fluorescent Amino Acid

Faculty Sponsor

Thomas Goyne


Arts and Sciences



ORCID Identifier(s)

Moriah Carmel: orcid.org/0000-0002-7073-6246 Hannah Laatsch: orcid.org/0000-0002-0919-5102

Document Type

Poster Presentation

Symposium Date

Summer 7-30-2018


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 from Laporte, IN. Hannah Laatsch is a senior Chemistry major from Janesville, WI. Dr. Goyne is an Associate Professor of Chemistry at Valparaiso University.

This document is currently not available here.