Chemistry, Department of

 

Department of Chemistry: Dissertations, Theses, and Student Research

First Advisor

Patrick H. Dussault

Date of this Version

4-2016

Document Type

Thesis

Citation

A thesis presented to the faculty of the Graduate College at the University of Nebraska in partial fulfillment of requirements for the degree of Master of Science

Major: Chemistry

Under the supervision of Professor Patrick H. Dussault

Lincoln, Nebraska, April 2016

Comments

Copyright © 2016, Benjamin D. Enns. Used by permission

Abstract

Our group is interested in cyclobutene analogs of fatty acids as reactive coatings, potential antibiotics, and as a new class of bioconjugate linkers. A convenient synthesis of this class of molecules was previously reported from our lab. However, ammonia, a key reagent in the earlier route, was recently reclassified as a highly corrosive gas requiring highly specialized equipment for storage and handling. The goal of this research was to find a convenient synthesis for the formation of cyclobutene that did not involve the use of ammonia. The other part of this thesis describes the preparation of a short chain cyclobutene fatty acid as a substrate for conjugation to an amino acid as part of a collaboration targeting the synthesis of proteins, which could be selectively modified using the cyclobutene/tetrazine "click" reaction.

Advisor: Patrick H. Dussault

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