Towards the Synthesis of 1,4-Dibenzyl-1,4,7-Triazacyclononane-7-Monoacetate for a Potential Mimic of Oxalate Degrading Enzymes

Date of Award

2010

Document Type

Thesis

Degree Name

Bachelors

Department

Natural Sciences

First Advisor

Sherman, Suzanne

Keywords

Oxalate, Bioinorganic Chemistry, Ligand Synthesis

Area of Concentration

Chemistry

Abstract

Oxalate oxidase and oxalate decarboxylase are enzymes responsible for the degradation of oxalate. These enzymes are present in plants, bacteria and fungi. Consumption of oxalate, by both people and livestock, can result in cardiological and kidney disease. This is because neither contains oxalate degrading enzymes. Small molecule mimics of oxalate oxidase and oxalate decarboxylase have the potential to function as a tool for understanding the activity of the enzymes, testing for oxalate toxicity, probing the relationship between structure and function, and much more. An oxalate oxidase or oxalate decarboxylase mimic requires the synthesis of a ligand for complexation with a manganese ion. Based on previous work in the Sherman lab and with collaborators, the novel ligand 1,4-dibenzyl-1,4,7-triazacyclononane-7-monoacetate is a new target ligand. A variety of routes were attempted to synthesize this ligand. The most successful synthetic route required the attachment of benzyl groups to N-tosyl-1,4,7-triazacyclo onane. However, the deprotection of the 1,4-dibenzyl-7-tosyl-1,4,7- triazacyclononane proved to be very difficult. A ligand nearly resembling the target ligand by 1H and 13CNMR has been synthesized. However, peculiarities in the data suggest that this ligand is likely not 1,4-dibenzyl-1,4,7-triazacyclononane-7-monoacetate. The following work describes the methods used towards the synthesis of the intended novel ligand.

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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