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The Synthesis and Characterization of Water Soluble Hydroindole-Based Nanostructures of Designed Three-Dimensional Architectures

by Habay, Stephen Anthony

Abstract (Summary)
This dissertation explores the design and synthesis of bis-amino acid molecular building blocks and their assembly into small oligomers of designed shape. Specifically, we investigated a class of monomer known as the hydroindole bis-amino acids. One member of this family, hin(2S4R7R9R), provided a sharp turn in three-dimensional space when assembled into oligomers. We employed various strategies to synthesize the hydroindole monomers, including a Diels-Alder pathway and an oxidative rearrangement of (L)-tyrosine. Larger oligomers containing this building block were modeled and found to have distinct compact tertiary structures. We then carried out the solid phase synthesis of these oligomers, composed of the hin(2S4R7R9R) and other monomers, and optimized their rigidification into spiro-ladder scaffolds of well defined architectures. Efforts towards full structural characterization of these molecules are also presented here. The hydroindole-based bis-amino acid building blocks are an integral part of a larger library of monomers that are used to construct water soluble macromolecules of designed shape. The ultimate goal of this new technology is to develop these macromolecules into functional nano-scale devices that display compact tertiary structures and present chemical functionality for use in a wide range of biomimetic and nanotechnology applications.
Bibliographical Information:

Advisor:Jeffrey D. Evanseck; Craig S. Wilcox; Christian E. Schafmeister; Kay M. Brummond

School:University of Pittsburgh

School Location:USA - Pennsylvania

Source Type:Master's Thesis

Keywords:chemistry

ISBN:

Date of Publication:03/20/2006

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