Synthesis of an Unnatural Fluorescent Amino Acid

Faculty Sponsor

Thomas Goyne


Arts and Sciences



ORCID Identifier(s)

0000-0001-8347-2748, 0000-0002-7189-0704, 0000-0003-2417-6986,

Presentation Type

Poster Presentation

Symposium Date

Spring 5-4-2017


"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.”1

Recent work has focused on: 1) using anhydrous reaction conditions to attach the allyl protecting group, 2) development of an assay to quantitate formaldehyde, and 3) exploring better methods to remove excess formaldehyde following the methylation reaction. The remaining tasks are to: 1) scale up the synthesis and 2) remove the two protecting groups.

1Stephen Sekoulopoulos, Thomas Goyne, “Phthalimide-Substituted Amino Acid, a Polarity-Sensitive Fluorophore.”

Poster presented in several venues during Fall 2016.

Biographical Information about Author(s)

Cody Steel is a biology and chemistry double major at Valparaiso University.

Thomas Goyne is a member of the chemistry faculty at Valparaiso University.

Yeongseo An is a senior biochemistry major at Valparaiso University.

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