Synthesis and Characterization of an Unnatural Fluorescent Amino Acid
Primary Submission Contact
Dr. Thomas Goyne
Faculty Sponsor Email Address
Arts and Sciences
Department of Chemistry
The goal of this project is to chemically synthesize a fluorescent amino acid that will later be used to build a protein that glows in the dark. Glow-in-the-dark proteins are of great value to biologists because fluorescent microscopy can then be used to observe the protein’s spatial and temporal location within a living cell. The specific objective of this project is to synthesize a 4-(N,N-dimethylamino) phthalimide-based environment-sensitive fluorescent amino acid. This will be accomplished by synthesizing two separate building blocks, 4-N,N-dimethylaminophthalic anhydride and allyl N-α-Fmoc-N-β-L-diaminopropionate, coupling them together and finally removing a protecting group. Synthesis of the pure anhydride required us to alter the published procedure in order to remove unreacted starting material. We have so far made both building blocks and have successfully practiced the coupling reaction using model compounds. As soon as this fluorescent amino acid is in hand, we plan to use a screening system to determine whether or not it can serve as a building block for proteins.
References: Trimoski, Blagojce and An, Yeongseo, "Synthesis and Characterization of an Unnatural Fluorescent Amino Acid" (2015). Celebration of Undergraduate Scholarship. Paper 446. http://scholar.valpo.edu/cus/446
An, Yeongseo and Trimoski, Blagojce, "Synthesis and Characterization of an Unnatural Fluorescent Amino Acid" (2015). Fall Interdisciplinary Research Symposium. Paper 37.
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