Riley Lewis

Date of Award

2019

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Area of Concentration

Chemistry

Abstract

Oxalate is a naturally occurring organic compound found in plants, bacteria, and fungi. In humans, excessive oxalate consumption is toxic and can cause numerous health issues such as kidney stones, and cardiological disorders. While humans do not contain any oxalate-degrading enzymes, many plants, bacteria, and fungi do. Two of the major oxalate digesting enzymes, oxalate oxidase (OXO) and oxalate decarboxylase (OxDc), contain manganese active sites responsible for catalytic activity, which can be of great interest to inorganic chemists. Not much is known about the mechanism of action for oxalate degradation, but deciphering it could have outstanding applications in the medical field and catalytic chemistry. Small enzyme models are much cheaper than the process of protein expression and purification, and can enable scientists to thoroughly analyze the active site through an analogue. Based on previous research conducted by Pecoraro et. al, and a recent publication detailing new methods for substituted triazacyclononane derivatives, 1,7-dibenzyl-1,4,7- triazacyclononane-n-acetate (Bn2TCMA) has become the target ligand for synthesizing an analogue of the OXO and OxDc active site. Triazacyclononane derivatives are shown to bind with manganese in a structurally similar way to the active sites of OXO and OxDc, making them an excellent ligand for this purpose. Progress was made towards synthesizing Bn2TCMA, but a number of errors precluded our ability to synthesize the final compound. We in turn thoroughly characterized one of the intermediates, and totally assigned the 1H and 13C NMR spectra. We synthesized Bn2TACN-EA, the ester form of Bn2TCMA, however, the 1H NMR spectrum showed impurities. Despite not successfully synthesizing Bn2TCMA, we now have a much better understanding of the synthetic pathway and can hopefully utilize this information for a complete synthesis. The complete synthesis of Bn2TCMA is definitely within reach, especially with newly found access to a solvent purification system and glove box to keep the reactions dry and air-free.

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