Peptidomimetic building blocks
for synthetic RNA ligands
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A well-known example of regulatory RNA-protein interaction is the complex of TAR-RNA of HIV-1 and the viral protein Tat. This complex is important for the efficient transcription of the viral genome. Knowledge of the principles of Tat to TAR RNA recognition should make it possible to design specific ligands that can attack as antiviral Tat antagonists. The aim of this thesis was the synthesis of RNA ligands for solid phase peptide synthesis (FPPS) based on heteroaromatic building blocks. The binding affinities of peptides and small molecules from the FPPS to the TAR RNA of HIV-1 were determine...
A well-known example of regulatory RNA-protein interaction is the complex of TAR-RNA of HIV-1 and the viral protein Tat. This complex is important for the efficient transcription of the viral genome. Knowledge of the principles of Tat to TAR RNA recognition should make it possible to design specific ligands that can attack as antiviral Tat antagonists. The aim of this thesis was the synthesis of RNA ligands for solid phase peptide synthesis (FPPS) based on heteroaromatic building blocks. The binding affinities of peptides and small molecules from the FPPS to the TAR RNA of HIV-1 were determined by fluorescence assay and fluorescence correlation spectroscopy (FCS). NMR studies and molecular dynamic calculations made it possible to detect a conformational change in TAR RNA. Antiviral properties of peptides and small molecules were determined by a HeLa P4 cell assay. A further goal of the work was the investigation of the binding concept and the antiviral properties of diaminopyrazoles and indazoles.
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