Title

Synthesis and Characterization of an Unnatural Fluorescent Amino Acid

Faculty Sponsor

Dr. Thomas Goyne

College

Arts and Sciences

Department/Program

Department of Chemistry

ORCID Identifier(s)

0000-0003-2417-6986

Document Type

Poster Presentation

Celebration Date

Summer 7-28-2015

Abstract

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.

Reference:

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

Biographical Information about Author(s)

Yeongseo An was born on April 3, 1995 in Gwangyang, South Korea. She came to the United States of America as an international student during her sophomore year of high school. She graduated from Illiana Christian High School in Lansing, Illinois, in 2013, with high honors. She started her undergraduate career at Valparaiso University in the fall of 2013. She is hoping to achieve her B.S. in Biochemistry and enroll in a graduate school to pursue a Ph.D.

Blagojce (Bill) Trimoski was born on May 23, 1995 in Ohrid, Macedonia. He moved to Crown Point, Indiana when he was about 2.5 years old and has grown up there since then. He graduated from Crown Point High School in 2013 with high honors. He started his undergraduate career at Valparaiso University in the fall of 2013 in pursuit of a B.S. in Biochemistry. He hopes to attend medical school immediately afterwards in pursuit of his M.D./Ph.D.

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