Date of Award

2013

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Oxalate, Triazacyclononane, Oxalate Oxidase

Area of Concentration

Chemistry, Biology

Abstract

Oxalate is a widely abundant compound found in a variety of plants, bacteria, and fungi. Oxalate is a toxic compound and excretion methods are limited in mammals because of the absence of oxalate-degrading enzymes. Accumulation of oxalate can occur via several routes, including genetic defects, dysfunctional fat absorption, excessive dietary consumption, or possibly deficiencies in metabolism of oxalate-precursors like glyoxal. Two manganese-containing metalloenzymes, oxalate oxidase (oxox) and oxalate decarboxylase (oxdc), are able to metabolize this toxic compound via an oxygen-dependent mechanism that is currently undetermined. A functional small molecule mimic of the active sites of oxox and oxdc could provide medicinal benefits to those suffering from hyperoxaluria and other associated conditions, such as calcium oxalate kidney stones. Based on previous work completed in the Sherman lab and with collaborators, the target ligand is 1,4-dibenzyl-1,4,7-triazacyclononane-7-acetate. Although progress has been problematic due to difficulty in removing the protecting tosyl group from the 1,4-dibenzyl-7-tosyl-1,4,7-triazacyclononane, previous students have effectively removed the group while maintaining the integrity of the benzyl groups. The next step in the synthesis, addition of the ethyl acetate arm, was successfully performed in this thesis in a small-scale reaction that was followed by nuclear magnetic resonance spectroscopy. The resulting hydrogen and carbon spectra provide evidence that the ethyl acetate arm was added to the ring. The following work describes the methods used towards the synthesis of the novel ligand.

Rights

The author has granted New College of Florida the nonexclusive right to archive, make accessible, and distribute for educational purposes this work in whole or in part in all forms of media, now or hereafter known. The copyright of this work remains with the author.

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