Self-assembly of functionalized synthetic nucleic acid bases

dc.contributor.advisorSessler, Jonathan L.en
dc.creatorJayawickramarajah, Janarthananen
dc.date.accessioned2008-08-28T22:24:47Zen
dc.date.available2008-08-28T22:24:47Zen
dc.date.issued2005en
dc.descriptiontexten
dc.description.abstractInspired by the significance and utility of hydrogen bond driven self-assembly, as exemplified through base-pairing interactions of double helical DNA, this dissertation discusses the synthetic preparation and structural analysis of a number of functionalized supramolecular ensembles derived from nucleic acid base-pairing. Specifically, three projects are detailed. Each of these projects, although under the general purview of basepairing, addresses a distinct issue in the field of molecular recognition. The first chapter will serve to introduce the general modalities of base-pairing as well as provide an overview of the diverse synthetic supramolecular ensembles that have been prepared by exploiting such interactions. Chapter 2 will detail the development and self-assembly properties of a novel guanosine-cytidine dinucleoside, which is capable of forming a cyclic ensemble through Watson-Crick hydrogen bonding. Chapter 3 will focus on the development of a porphyrin-fullerene derived photoinduced electron transfer model system, which self-assembles via Watson-Crick base-pairing interactions. Chapter 4 will introduce a new pyrrole-tethered purine nucleoside, which is capable of forming an extended three-point Hoogsteen-type base-pairing interaction with guanosine. In addition, this chapter will also investigate the capability of this purine derivative in disrupting guanosine-derived self-association. At the end of each of these chapters, a section pertaining to ongoing efforts and proposed future research is included. Chapter 5 provides experimental methods and characterization data.
dc.description.departmentChemistry and Biochemistryen
dc.description.departmentChemistryen
dc.format.mediumelectronicen
dc.identifierb60769749en
dc.identifier.oclc67835579en
dc.identifier.urihttp://hdl.handle.net/2152/1943en
dc.language.isoengen
dc.rightsCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.en
dc.subject.lcshNucleic acidsen
dc.subject.lcshOrganic compounds--Synthesisen
dc.titleSelf-assembly of functionalized synthetic nucleic acid basesen
dc.type.genreThesisen
thesis.degree.departmentChemistryen
thesis.degree.disciplineChemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen
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