Date of Award

2012

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne E.

Keywords

Oxalate Oxidase, Hyperoxaluria, Biological Mimic

Area of Concentration

Chemistry

Abstract

The enzymes oxalate oxidase (oxox) and oxalate decarboxylase (oxdc) are manganese-containing supercupins that have the unique ability to degrade oxalate. These oxalate-degrading enzymes are present in plants, fungi, and bacteria but not in mammals. Both overconsumption of oxalate rich foods and increased endogenous oxalate production as a result of inborn errors of glyoxalate metabolism result in a disorder called hyperoxaluria. The consequences of hyperoxaluria, renal failure and cardiac conditions, are detrimental if left untreated. Hyperoxaluria is detected in an enzymatic assay that utilizes oxalate oxidase to measure urinary oxalate. A lower cost alternative would be to utilize a small molecular mimic that has a similar structure to the active sites of oxox and oxdc. If the mimic is non-toxic, it could even be implemented to treat the various health effects of hyperoxaluria or treat industrial wastewater, which is often polluted with oxalate. Moreover, a functional mimic of these enzymes may help unravel the mechanisms by which they degrade oxalate. To structurally and functionally model the active sites of oxox and oxdc, the target ligand is 1,4-dibenzyl-1,4,7-triazocyclanonane-7-monoacetate (Bn2TCMA). The synthesis of the ligand, Bn2TCMA, was brought further than its antepenultimate step. Deprotection of the final tosyl protecting group was achieved using a solution of sodium and naphthalene to yield 1,4-dibenzyl-1,4,7-triazacyclononane (Bn2TACN) as an oil. Upon crystallization of the oil from actetone, a relatively clean solid product was obtained.

Rights

This bibliographic record is available under the Creative Commons CC0 public domain dedication. The New College of Florida, as creator of this bibliographic record, has waived all rights to it worldwide under copyright law, including all related and neighboring rights, to the extent allowed by law.

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