Difference between revisions of "Chemical, Enzymatic, and Electrochemical Oxidation of Biophenols"

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==Introduction==
 
==Introduction==
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HPA is a monocarboxilic acid and a member of the phenol family. In industry, HPA serves as a common precursor to the synthesis of drugs and pesticides due to its simplicity in structure (figure 1) (1,2). HPA is an important metabolite for anaerobic and aerobic bacteria alike....(3,4)
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As a phenol, HPA is able to undergo a one electron oxidation with an appropriate oxidizing agent to generate the radical shown in figure 2. This oxidative radical will couple to other molecules to form dimers, trimmers, and heavier polymers. HPA will readily undergo radical polymerization when met with the appropriate conditions. Common oxidation techniques employed to generate the radical include doing so chemically, electrochemically, and enzymatically.
  
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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.
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Electrochemical, enzymatic, and chemical oxidation data is shown for HPA in this paper and the oxidation product outcomes are compared. Initial data for the more complex tyrosine and N-acetyl tyrosine is also presented.
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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.
 
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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.
 
  
 
==Materials and Methods==
 
==Materials and Methods==

Revision as of 23:26, 13 May 2022

Abstract

Introduction

HPA is a monocarboxilic acid and a member of the phenol family. In industry, HPA serves as a common precursor to the synthesis of drugs and pesticides due to its simplicity in structure (figure 1) (1,2). HPA is an important metabolite for anaerobic and aerobic bacteria alike....(3,4) As a phenol, HPA is able to undergo a one electron oxidation with an appropriate oxidizing agent to generate the radical shown in figure 2. This oxidative radical will couple to other molecules to form dimers, trimmers, and heavier polymers. HPA will readily undergo radical polymerization when met with the appropriate conditions. Common oxidation techniques employed to generate the radical include doing so chemically, electrochemically, and enzymatically.

Electrochemical, enzymatic, and chemical oxidation data is shown for HPA in this paper and the oxidation product outcomes are compared. Initial data for the more complex tyrosine and N-acetyl tyrosine is also presented.

Materials and Methods

Results

Discussion

References

Page History

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

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