Date of Award

5-2026

Document Type

Thesis

Degree Name

Bachelor of Arts (BA)

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Area of Concentration

Chemistry

Abstract

Oxalate is a naturally occurring compound that can be toxic to humans at high concentrations as humans lack the oxalate degrading enzymes found in plants, fungi and bacteria. Key enzymes involved in oxalate metabolism are oxalate oxidase and oxalate decarboxylase, both of which are manganese based metalloenzymes. Due to limited research, much is unknown regarding their mechanism of action ,with multiple proposals reported, but no unified consensus. Synthetic model complexes are commonly used to probe the function of metalloenzymes by replicating structural and electronic features in simplified systems. In biomimicry, 1,4,7,-triazacyclononane (TACN) has attracted attention for its N3O donor set and ability to be functionalized. Based on literature analysis, 1,4-dibenzyl-1,4,7,-triazcyclononane-7-monoacetate (Bn2TCMA) was identified as a promising ligand to model oxalate degrading enzymes. This study explores synthetic routes towards Bn2TCMA including a previously reported pathway and an adaptation of a recently developed route. The older route was limited by persistent issues in tosyl deprotection, whereas the newer approach indicated its simplicity and potential effectiveness. Although the target compound was not fully attained, results provide evidence that support the continuation of the modern pathway.

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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