Albert Lee

Date of Award

2015

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Oxalates, Oxalate Oxidase, Oxalate Decarboxylase, Ligands

Area of Concentration

Chemistry

Abstract

Oxalate is a toxic compound found primarily in plants. Humans lack oxalate-degrading enzymes, and the accumulation of large quantities of this compound may lead to oxalate poisoning, which in turn may cause cardiological diseases and kidney stones. Oxalate oxidase and oxalate decarboxylase are two manganese-containing enzymes found in many plants that are able to metabolize oxalate. The synthesis and characterization of small molecule functional models that very closely mimic the active sites of these oxalate-degrading enzymes may help overcome problems associated with the study of more complex enzymatic systems, particularly the elucidation of their mechanisms. Furthermore, there are potential medical benefits associated with a functional model, including the diagnosis and treatment of oxalate poisoning and related diseases, such as hyperoxaluria. Based on previous work of the Sherman and Pecoraro labs, the synthetic target was the manganese (II) complex of the N3O donor ligand 1,4-diisopropyl-1,4,7-triazacyclononane-7-monoacetate (iPr2TCMA). This previously synthesized ligand was reproduced in this work in order to further study the complex’s reactivity with oxalate. This work provides the first successful synthesis of this ligand in the Sherman laboratory, after prior attempts by two previous students. The following work describes the methods used towards the synthesis of the ligand.

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