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https://hdl.handle.net/2142/84405
Description
Title
Molecular Recognition of Nucleic Acids
Author(s)
Thiessen, Paul Archer
Issue Date
1998
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)
Biology, Molecular
Language
eng
Abstract
Part II presents the design and attempted synthesis of several novel nucleosides that were intended to hydrogen bond to Watson-Crick base pairs in the major groove of DNA. The geometry of the connection of these heterocycles to the ribose backbone was designed to be isomorphous with the T$\cdot$AT and C$\sp+\cdot$GC base triplets of the Pyr$\cdot$Pur-Pyr triplex motif. The goal of this work was to improve the sequence generality of triple helix formation. In some cases the heterocycles could not be made, while in others the desired heterocycles were made, but attachment to the ribose for incorporation into DNA oligonucleotides was unsuccessful. Friedlander condensation with tetramic acids was shown to be a viable method for construction of the tricyclic portion of a CG host.
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