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Reactivity Studies on Coenzyme Model Compounds

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Title: Reactivity Studies on Coenzyme Model Compounds
Author: Milutinovich, Nicholas
Department: Department of Chemistry
Program: Chemistry
Advisor: Denk, Michael
Abstract: Hydride transfer is an elementary biochemical step performed by coenzymes like methylenetetrahydrofolate (MTHF) and nicotinamide adenine dinucleotide (NADH). This thesis describes the discovery of a new reactivity of MTHF and NADH model compounds in the reductive dehalogenation of halocarbons. Formal hydride transfer from the model compounds reduces halocarbons, mimicking the well-known in vivo reducing activity of the biomolecules themselves. The reactions are capable of dehalogenating a variety of halocarbons under biomimetic conditions in the presence of air and water including those with toxicological and environmental relevance. Investigations of the notorious pesticide DDT and the inhalation anesthetic and greenhouse molecule halothane demonstrated rapid conversion to known in vivo metabolites, which suggests the involvement of MTHF and NADH in the still obscure metabolic degradation of both compounds. Conversely, the depletion of MTHF and NADH models by halocarbons suggests a new toxicological activity of these molecules.
Date: 2018-01-05

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