Synthesis and Characterization of a 4-(N,N-dimethylamino) Phthalimide-Substituted Amino Acid, a Polarity-Sensitive Fluorophore

Authors

Stephen Sekoulopoulos, Valparaiso UniversityFollow
Ashita Bhatnagar, Valparaiso UniversityFollow

Faculty Sponsor

Thomas Goyne

College

Arts and Sciences

Discipline(s)

Department of Chemistry

Presentation Type

Poster Presentation

Symposium Date

Summer 7-28-2016

Abstract

The goal of this project is to chemically synthesize a fluorescent amino acid that will later be used as a glow-in-the-dark building block for proteins. The resulting 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 the phthalimide-based environment-sensitive fluorescent amino acid shown in the equation below. We have synthesized and coupled the two building blocks and have characterized the coupled product by liquid chromatography mass spectroscopy (LC-MS), ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy. The remaining task is to remove the two protecting groups.

Biographical Information about Author(s)

Stephen is a junior biochemistry major at Valparaiso University and a member of Christ College Honors College. This is his second summer conducting research at Valparaiso and his first summer working with the chemistry department. After graduation, he plans to attend medical school in hopes of specializing in pediatric neurosurgery.

Recommended Citation

Sekoulopoulos, Stephen and Bhatnagar, Ashita, "Synthesis and Characterization of a 4-(N,N-dimethylamino) Phthalimide-Substituted Amino Acid, a Polarity-Sensitive Fluorophore" (2016). Symposium on Undergraduate Research and Creative Expression (SOURCE). 566.
https://scholar.valpo.edu/cus/566