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Bromination of Phenylalanine via Organic Electrosynthesis

Semester: Summer 2023

Presentation description

The bromination of amino acids is used in the pharmaceutical industry to tag drug molecules for the purpose of increasing their detection and membrane permeability. However, traditional methods require the use of environmentally-unfriendly chlorinated solvents and harsh organic oxidants. In our research, an electrochemical synthetic method called ""reductive oxidation,"" which is based on prior work from the White lab, is being investigated as a method for bromination. Reductive oxidation is performed in an aqueous solution and uses an inorganic electrocatalyst to generate a strong oxidizing radical. The radical then activates and oxidizes the amino acid, allowing for the bromination to follow. In this work, reductive oxidation is used to generate the sulfate radical anion (SO4-·), which abstracts a hydrogen atom from phenylalanine. In the presence of carbon tetrabromide, the phenylalanine radical is brominated. Cyclic voltammetry indicates that hydrogen atom abstraction from phenylalanine occurs as the results are consistent with prior experiments. While recovery of the brominated phenylalanine is still underway, this method may prove as an acceptable and environmentally-friendly substitute for the bromination of amino acids.

Presenter Name: Robert Winzerling
Presentation Type: Poster
Presentation Format: In Person
Presentation #119
College: Science
School / Department: Chemistry
Research Mentor: Henry White
Date | Time: Thursday, Aug 3rd | 10:30 AM