Date of Award

2014

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Synthetic Models, Chemistry, Ligand

Area of Concentration

Chemistry

Abstract

The exact mechanisms by which oxalate oxidase and oxalate decarboxylase degrade oxalate are still debated. The development of a small synthetic model of the active site may allow for this to be studied further. The target ligand, 1,4-dibenzyl-1,4,7-triazacyclononane-7-monoacetate (Bn2TCMA), was designed for this purpose. The addition of the benzyl groups is predicted to add enough steric hindrance to the ligand to prevent multiple ligands from bonding to the manganese ion. The benzyl groups also have the added advantage of being easily altered to include different electron withdrawing groups and electron donating groups to fine tune the redox chemistry. The synthesis of Bn2TCMA is complicated by the difficulty in removing the tosyl group from 1,4-dibenzyl-7-tosyl-1,4,7-triazacyclononane; percent yields have been consistently low. Progress towards the synthesis of Bn2TCMA has been made by the successful purification of 1,4-dibenzyl-1,4,7-triazacyclononane-7-ethyl acetate (Bn2TACN-EA) after the addition of the ethyl acetate arm. Percent yields of 15.1% and 81.5 % were obtained for the first time for 1,4-dibenzyl-1,4,7-triazacyclononane (Bn2TACN) and Bn2TACN-EA, respectively. The final synthetic step, the addition of potassium hydroxide for the removal of the ethyl group has been performed and the product studied by 1H-NMR and 13C-NMR.

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