Using guanidinium groups for the recognition of RNA and as catalysts for the hydrolysis of RNA

Article abstract of DOI:10.1016/S0968-0896(97)00051-5

The guanidinium functional group is commonly used in nature to recognize and bind anions through ion pairing and hydrogen bonding. Specific hydrogen-bonding patterns can be found in crystal structures of simple guanidinium salts. Analysis of these simple salts reveals a variety of features which are found in natural systems. These features have been applied to a series of artificial phosphodiesterases for RNA. These receptors incorporate guanidinium groups positioned to mimic the hydrogen-bonding patterns found in simple guanidinium salts and natural enzymes. This paper outlines general guanidinium hydrogen-bonding patterns. Next, the complexation of phosphodiesters with a series of artificial receptors are analyzed in terms of counterions, solvent mixtures, and cavity flexibility. In addition, strategies to enhance catalysis through a pK(a) analysis of phosphoranes are addressed. Next, we describe how our findings were incorporated into second generation receptors/catalysts. Finally, our future work is discussed.