Part I. A Stacked Intercalator Approach to Selectively Target Mismatches Within CTG and CUG Trinucleotide Repeats. Part II. Aromatic Stacking of Naphthoyl Modified Cytosines Within PNA·DNA Duplexes
Arambula, Jonathan
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Permalink
https://hdl.handle.net/2142/84339
Description
Title
Part I. A Stacked Intercalator Approach to Selectively Target Mismatches Within CTG and CUG Trinucleotide Repeats. Part II. Aromatic Stacking of Naphthoyl Modified Cytosines Within PNA·DNA Duplexes
Author(s)
Arambula, Jonathan
Issue Date
2008
Doctoral Committee Chair(s)
Zimmerman, Steven C.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
To this end, naphthoyl substituted cytosines were synthesized and incorporated into PNA monomers followed by preparation of PNA oligomers containing multiple substitutions of the modified cytosine. Thermal denaturation studies and thermodynamic analyses of resulting PNA·DNA duplexes were performed to determine the stabilization due to added stacking between the naphthoyl substituents aligned within the major groove. PNA·DNA duplex stabilization was observed when three naphthoyl substitutions were aligned when compared to the same PNA·DNA duplex with separated naphthoyl substituents; however, an overall destabilization was observed when compared to the unsubstituted PNA·DNA duplex. Future modifications are considered to enhance the overall stability of PNA·DNA duplexes containing modified nucleosides.
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