Author

Ashley Burns

Date of Award

12-2019

Degree Type

Honors College Thesis

Department

Chemistry and Biochemistry

First Advisor

Karl Wallace, Ph.D.

Advisor Department

Chemistry and Biochemistry

Abstract

Siderophores are molecules capable of binding ferric ions with high affinity (Ka = 1052). This thesis outlines our attempts to synthesize an artificial siderophore, which incorporates a signaling group to help monitor the uptake of ferric ions. The artificial siderophore is a tripodal molecular receptor synthesized in a five-step procedure with a proposed final sixth step. Rhodamine 6G azide (95.0% yield) was formed from rhodamine 6G and the synthesis of 2-azidoethanamine was modified from the literature. The tripodal arm portion of the sensor was successfully synthesized by protecting the catechol of 2,3-dihydroxybenzaldehyde to form 3-formyl-1,2-phenylene dimethanesulfonate (98.8% yield). The reduction of the aldehyde in the previous compound to a primary alcohol formed 3-(hydroxymethyl)-1,2-phenylene dimethanesulfonate (86.6% yield), which then underwent a nucleophilic substitution to yield 3-(bromomethyl)-1,2-phenylene dimethanesulfonate (80.0% yield). The product of the nucleophilic substitution then successfully underwent a bimolecular nucleophilic substitution to yield the mesyl protected tripodal arm (76.8% yield).

Available for download on Thursday, January 14, 2021

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