Synthesis of Oxygenated Hydrocarbons by Cytochrome P-450 Electroenzymology

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Vincent Vilker 9313009 This work is directed toward development of an economical synthesis of oxygenated hydrocarbons using active cytochrome P-450 immobilized on a working electrode. The immediate objectives are to determine stoichiometries, product distributions, and kinetics of the hydroxylation of hydrocarbons by NADH-driven P-450, to develop modified electrodes for the regeneration of P-450, and to compare products, rates, and yields of the NADH and electrochemically regenerated cytochrome P-450. Two forms of cytochrome are studied: P-450cam and P-450soy; the similarities and differences are examined. Hydrocarbon substrates include norcamphor, -pinene, 1,2,3,4-tetrahydronaphthalene (tetralin), decahydronaphthalene (decalin), and naphthalene. Regiospecificity and stereospecificity are examined, turnover rates on the cytochrome are measured, and models of the process are developed. This should lead to an energy-efficient bioelectrochemical process that combines the efficiency of electrocatalysts with the specificity of enzymes, thus producing good yields of high-value products with little unwanted side reaction. The project is done in collaboration with the duPont Company.