A selective recognition mode of a nucleic acid base by an aromatic amino acid: L-phenylalanine-7-methylguanosine 5'-monophosphate stacking interaction
- 11 July 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 16 (13) , 6175-6190
- https://doi.org/10.1093/nar/16.13.6175
Abstract
The conformation of 7-methylguanosine 5′-monophosphate (m7GMP) and its interaction with L-phenylalanine (Phe) have been investigated by X-ray crystallographic, H-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) quarternization 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.Keywords
This publication has 13 references indexed in Scilit:
- Stacking and hydrogen bonding interactions between phenylalanine and guanine nucleotide: Crystal structure of L-phenylalanine-7-methylguanosine-5′-monophosphate complexBiochemical and Biophysical Research Communications, 1986
- Structural analysis of the messenger RNA cap-binding protein. Presence of phosphate, sulfhydryl, and disulfide groups.Journal of Biological Chemistry, 1986
- The stacking interactions in 7-methylguanine-tryptophan systems, a model study for the interaction between the ‘cap’ structure of mRNA and its binding proteinBiochemical and Biophysical Research Communications, 1983
- Interactions between functional groups in protein-nucleic acid associationsProgress in Biophysics and Molecular Biology, 1982
- Interactions of Oligopeptides With Nucleic AcidCritical Reviews in Biochemistry, 1981
- Selective recognition of nucleic acids by proteins: the specificity of guanine interaction with carboxylate ions.Proceedings of the National Academy of Sciences, 1977
- A relation between inhibition of protein synthesis and conformation of 5′-phosphorylated 7-methylguanosine derivativesJournal of Molecular Biology, 1977
- Nuclear magnetic resonance studies of 5'-ribo- and deoxyribonucleotide structures in solutionBiochemistry, 1974
- Molecular orbital calculations on the conformation of nucleic acids and their constituents VI. Conformation about the exocyclic C(4′)-C(5′) bond in α-nucleosidesBiochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, 1973
- ELECTRON-DONOR AND -ACCEPTOR PROPERTIES OF BIOLOGICALLY IMPORTANT PURINES, PYRIMIDINES, PTERIDINES, FLAVINS, AND AROMATIC AMINO ACIDSProceedings of the National Academy of Sciences, 1958