Chemical, Enzymatic, and Electrochemical Oxidation of Biophenols

Introduction

Phenols such as 4-hydroxyphenylacetic acid, N acetyl tyrosine, tyrosine, and diiodotyrosine have various attractive bioactivities, which broadly classifies them as 'biophenols'. 4-Hydroxyphenylacetic acid (HPA) is an important precursor for the synthesis of drugs, pesticides, and biochemicals (). The redox properties of these phenols can be studied using chemical, enzymatic, and electrochemical methods. will discuss HRP and KMnO4 methods.

This project aims to enzymatically and chemically oxidize HPA with the methods described previously. Whereas chemical and enzymatic methods have a fixed oxidation potential, electrochemical methods allow for control of the oxidation potential. While HPA and N acetyl tyrosine have oxidation potentials capable of being reached by HRP, this is not the case for diiodotyrosine, whose oxidation potential lies outside this range. For diiodotyrosine, cyclic voltammetry studies coupled with subsequent bulk electrolysis will be utilized instead. The oxidation products will be monitored with HPLC and isolated via flash chromatography. Oxidation products with be characterized with HNMR and HR-MS.

From early investigations in this study, it appears the shelf lives of these biophenols are very short lived; for contaminants have been spotted with HPLC. These contaminants will be investigated with further HPLC studies and H NMR, and if applicable, purification techniques will be utilized.

Page History

This page was created by Sara L. Simonson in the fall of 2021