Date of Award

8-2007

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

Richard Pagni, Bin Zhao, Narendra Dahotre

Abstract

Boron neutron capture therapy (BNCT) is a binary form of cancer treatment wherein 10B nuclei, when irradiated with thermal neutrons, produce high energy transfer particles. These particles, due to their size and energy, are confined to a radius of 9-10μm, which is comparable to the size of single cell. Potential BNCT agents reported in the literature include boron-containing amino acids, nucleic acids, nucleosides, antibodies, and other biomolecules.

In recent years, microwaves have gained importance in organic chemistry. Microwave induced reactions are energy efficient, often enhance reaction rates, and generally lead to enhanced product yields. Recent studies have shown that potassium organotrifluoroborates offer solutions to a number of problems that sometime occur in organoboron coupling reactions.

This dissertation describes the synthesis of novel unnatural boronated amino acids as potential BNCT agents. The new microwave enhanced synthetic methodologies developed in this dissertation are important transformations in modern organic chemistry. Mild reaction conditions, short reaction times, and tolerance for various functional groups are advantages of these methodologies.

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Chemistry Commons

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