title: A selective recognition mode of a nucleic acid base by an aromatic amino acid: L-phenylalanine-7-methylguanosine 5'-monophosphate stacking interaction.
abstract: The conformation of 7-methylguanosine 5'-monophosphate (m7GMP) and its interaction with L-phenylalanine (Phe) have been investigated by X-ray crystallographic, 1H-nuclear magnetic resonance, and energy calculation methods. The N(7) methylation of the guanine base shifts m7GMP toward an anti--gauche, gauche conformation about the glycosyl and exocyclic C(4')-C(5') bonds, respectively. The prominent stacking observed between the benzene ring of Phe and guanine base of m7GMP is primarily due to the N(7) guarternization of the guanine base. The formation of a hydrogen bonding pair between the anionic carboxyl group and the guanine base further stabilizes this stacking interaction. The present results imply the importance of aromatic amino acids as a hallmark for the selective recognition of a nucleic acid base.
authors.affiliation: Laboratory of Physical Chemistry, Osaka University of Pharmaceutical Sciences, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Ishida
authors.forename: M
authors.initials: M
authors.lastname: Doi
authors.forename: M
authors.initials: M
authors.lastname: Inoue
mesh_terms: D003461:Crystallography; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D010649:Phenylalanine / Q000378:metabolism*; D012314:RNA Cap Analogs / Q000378:metabolism*; D012315:RNA Caps / Q000378:metabolism*; D014961:X-Ray Diffraction
chemical_list: D012314:RNA Cap Analogs; D012315:RNA Caps; C011925:7-methylguanosine-5'-monophosphate; D010649:Phenylalanine