Part I. The Synthesis and Study of Luminescent Polyglycerol Dendrimers. Part II. Adenine Receptors With Simultaneous Watson-Crick and Hoogsteen Binding
McKay, Jonathan
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https://hdl.handle.net/2142/84274
Description
Title
Part I. The Synthesis and Study of Luminescent Polyglycerol Dendrimers. Part II. Adenine Receptors With Simultaneous Watson-Crick and Hoogsteen Binding
Author(s)
McKay, Jonathan
Issue Date
2007
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
"Part II discusses efforts to synthesize receptors that employ hydrogen bonds to both the Hoogsteen and Watson-Crick faces of adenine as a means of enhancing the molecular recognition of this important biomolecule. A number of design approaches were carried out to ""clamp"" the exocyclic amine group of adenine. Model studies in chloroform as well as computer modeling demonstrated that multiple contacts on each face were necessary to obtain increased affinity over Nature's chosen hydrogen-bonding partner to adenine, thymine. A promising bicyclic ligand for adenine was synthesized using this approach."
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