The Utility of 7-Deazaguanine: Part I. High Affinity, High Fidelity Modules for Supramolecular Chemistry, And, Part II. Molecular Recognition of Uracil and Thymine
Ong, Hugo Calvin
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https://hdl.handle.net/2142/84277
Description
Title
The Utility of 7-Deazaguanine: Part I. High Affinity, High Fidelity Modules for Supramolecular Chemistry, And, Part II. Molecular Recognition of Uracil and Thymine
Author(s)
Ong, Hugo Calvin
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
A water-soluble analogue of the 2-naphthyl-7-DeG host was synthesized and evaluated as a molecular recognition unit to a thymine (T) bulge of a short 10-bp oligomer. The ligand was found to stabilize the T bulge quite significantly (+7.8°C) relative to the C bulge (3.6°C) and A and G bulges (≤ 2.0°C) at 5.0 equivalents, when the bulged base was flanked by guanosines (G's). Furthermore, the ligand did not stabilize the normal duplex under any condition. Control studies suggest that the ligand binds C primarily by intercalation, but binds T by intercalation and hydrogen-bonding. Isothermal titration calorimetry experiments gave a K d of 5.4 +/- 0.6 muM to the T bulge.
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