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

Habay, Stephen Anthony (2006) The Synthesis and Characterization of Water Soluble Hydroindole-Based Nanostructures of Designed Three-Dimensional Architectures. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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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.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Habay, Stephen Anthonysah20@pitt.eduSAH20
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairSchafmeister, Christian Emeister@pitt.eduMEISTER
Committee MemberWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberEvanseck, Jeffrey
Committee MemberBrummond, Kay Mkbrummon@pitt.eduKBRUMMON
Date: 20 March 2006
Date Type: Completion
Defense Date: 28 November 2005
Approval Date: 20 March 2006
Submission Date: 21 October 2005
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: NMR; tertiary structure; macromolecules; peptide synthesis
Other ID:, etd-10212005-152107
Date Deposited: 10 Nov 2011 20:03
Last Modified: 15 Nov 2016 13:50


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