Taylor Sweet

Date of Award

2015

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Oxalates, Ligands, Oxalate Degradation, Synthetic Models

Area of Concentration

Chemistry

Abstract

Oxalate is a toxic compound present in plant, fungi, and bacteria. These organisms use oxalate-degrading enzymes, including two manganese enzymes, oxalate decarboxylase and oxalate oxidase. Oxalate is widely consumed in normal human diets as it is found in fruits, vegetables, and wheat grains. Mammals lack oxalate-degrading enzymes, and accumulation of oxalate can lead to serious pathologic conditions such as edema, hyperoxaluria (excessive urinary excretion of oxalate), which can lead to renal failure, urolithiasis (calcium oxalate stones located anywhere within the urinary tract, including kidney and bladder stones), and cardiomyopathy (abnormal heart muscle). Besides the health concerns than can be caused by oxalate, precipitation of calcium oxalate (known as scaling) is a current concern in the pulp and paper industry. Small synthetic functional models for oxalate degrading enzymes could lead to information about their mechanisms for oxalate degradation, as there is currently much debate on these. Functional models could also have potential pharmaceutical and industrial applications. In this work, research towards the synthesis of two new tetradentate N3O donor ligands 1,4- diphenyl-1,4,7-triazacyclononane-7-monoacetate (Ph2TCMA) and 1,4-dipyridyl-1,4,7-triazacyclononane-7-monoacetate (Py2TCMA), for use in synthetic models of oxalate oxidase and oxalate decarboxylase, are described. The synthesis of TACNts (ts=tosyl) was accomplished. Addition of either phenyl or pyridyl groups to the two unprotected nitrogen atoms of triazacylcononane was attempted. Further experimental work is needed to complete the syntheses of these ligands.

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