DOI
https://doi.org/10.25772/E68W-ZM15
Defense Date
2009
Document Type
Thesis
Degree Name
Master of Science
Department
Chemistry
First Advisor
Dr. Nicholas Farrell
Abstract
Non-covalent interactions involving π-π stacking play an essential role in self-assembly and molecular recognition processes such as protein folding and DNA/RNA-protein selective recognition. The knowledge gained from these studies could provide insight into possible site recognition complexes, inhibiting or mimicking protein-protein or protein-DNA interactions. Based on molecular modeling as well as HOMO and LUMO energies, several chromophores were selected with a variety of ∆ε values (∆ε= |εHOMO,NAcTrp – εLUMO,chromophores|), high and low, to establish a correlating trend with the modeling and experimental data. The corresponding Pt(dien) compounds were synthesized and their ability to stack to N-acetyl tryptophan was evaluated by fluorescence quench experiments. Attaching a strong electron donating/withdrawing group or extending the π system of pyridine or thiazole by means of a benzene ring (quinoline and benzothiazole) was found to enhance the π-π interaction with N-acetyl tryptophan.
Rights
© The Author
Is Part Of
VCU University Archives
Is Part Of
VCU Theses and Dissertations
Date of Submission
12-11-2009