title: Using guanidinium groups for the recognition of RNA and as catalysts for the hydrolysis of RNA.
abstract: 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 pKa analysis of phosphoranes are addressed. Next, we describe how our findings were incorporated into second generation receptors/catalysts. Finally, our future work is discussed.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin 78712, USA.
authors.forename: D M
authors.initials: DM
authors.lastname: Perreault
authors.forename: L A
authors.initials: LA
authors.lastname: Cabell
authors.forename: E V
authors.initials: EV
authors.lastname: Anslyn
mesh_terms: D002384:Catalysis; D004247:DNA / Q000378:metabolism; D015696:Gene Products, tat / Q000378:metabolism; D019791:Guanidine; D006146:Guanidines / Q000378:metabolism*; D006860:Hydrogen Bonding; D006868:Hydrolysis; D007700:Kinetics; D008836:Micrococcal Nuclease / Q000378:metabolism; D009690:Nucleic Acid Conformation; D012313:RNA / Q000378:metabolism*; D012367:RNA, Viral / Q000378:metabolism; D015533:Transcriptional Activation
chemical_list: D015696:Gene Products, tat; D006146:Guanidines; D012367:RNA, Viral; D012313:RNA; D004247:DNA; D008836:Micrococcal Nuclease; D019791:Guanidine