Presentation Title

Cobalticinium Derivatives as Mediators for Bioelectrochemical Catalysis with P450

Start Date

November 2016

End Date

November 2016

Location

HUB 302-37

Type of Presentation

Poster

Abstract

Cobalticinium Derivatives as Mediators for Bioelectrochemical Catalysis with P450

The enzyme cytochrome P450 from Bacillus megaterium (BM3) is a fatty acid hydroxylase that is capable of performing selective oxygenations under physiological conditions. In the human body, it resides in the liver to eliminate xenobiotics and create hormones. This activity has several applications in biotechnology and drug development. However, industrial use of the enzyme is impractical because it requires electrons from the molecule NADPH which is both expensive ($100,000/mol) and has limited stability. Cobalticinium salts show great potential to substitute for NADPH in a bioelectrochemical system: they readily accept electrons from electrodes, their very negative reduction potential makes them powerful reductants, and they remain stable even under unfavorable conditions of mineral acids and aqueous base.

The proposed research involves an integration of biological procedures to make the enzyme, organometallic synthesis of the cobalticinium mediator, and electrochemistry to develop the biocatalytic system; the major experimental endeavors are making cobalticinium salts and conjugating the compounds to the P450 enzyme. Multiple synthetic pathways were explored to make carboxylic acid cobalticinium and ethynylcobalticinium, which differed in solubility, functional groups, and redox potential. Experimentation with cobalticinium derivatives will continue in order to find the ideal molecule to act as an electron transfer mediator between the electrode and the enzyme. Once it is appropriately conjugated, the cobalticinium salt will relay electrons to P450 in the presence of a graphite electrode. The completed system will effectively provide electrons to the protein thus giving an opportunity for catalytic substrate oxidation.

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Nov 12th, 1:00 PM Nov 12th, 2:00 PM

Cobalticinium Derivatives as Mediators for Bioelectrochemical Catalysis with P450

HUB 302-37

Cobalticinium Derivatives as Mediators for Bioelectrochemical Catalysis with P450

The enzyme cytochrome P450 from Bacillus megaterium (BM3) is a fatty acid hydroxylase that is capable of performing selective oxygenations under physiological conditions. In the human body, it resides in the liver to eliminate xenobiotics and create hormones. This activity has several applications in biotechnology and drug development. However, industrial use of the enzyme is impractical because it requires electrons from the molecule NADPH which is both expensive ($100,000/mol) and has limited stability. Cobalticinium salts show great potential to substitute for NADPH in a bioelectrochemical system: they readily accept electrons from electrodes, their very negative reduction potential makes them powerful reductants, and they remain stable even under unfavorable conditions of mineral acids and aqueous base.

The proposed research involves an integration of biological procedures to make the enzyme, organometallic synthesis of the cobalticinium mediator, and electrochemistry to develop the biocatalytic system; the major experimental endeavors are making cobalticinium salts and conjugating the compounds to the P450 enzyme. Multiple synthetic pathways were explored to make carboxylic acid cobalticinium and ethynylcobalticinium, which differed in solubility, functional groups, and redox potential. Experimentation with cobalticinium derivatives will continue in order to find the ideal molecule to act as an electron transfer mediator between the electrode and the enzyme. Once it is appropriately conjugated, the cobalticinium salt will relay electrons to P450 in the presence of a graphite electrode. The completed system will effectively provide electrons to the protein thus giving an opportunity for catalytic substrate oxidation.