STRUCTURAL STUDIES OF THE INTERACTION BETWEEN INDOLE-DERIVATIVES AND BIOLOGICALLY IMPORTANT AROMATIC-COMPOUNDS .21. PROMINENT STACKING INTERACTION WITH AROMATIC AMINO-ACID BY N-QUARTERNIZATION OF NUCLEIC-ACID BASE - X-RAY CRYSTALLOGRAPHIC CHARACTERISTICS AND BIOLOGICAL IMPLICATIONS

In order to investigate the mode of interaction between the N-quarternized cytosine base and the aromatic amino acid, the crystal structure of the 3-methylcytidine-5′-monophosphate: tryptamine complex was analyzed by X-ray diffraction. The complex crystals were stabilized by extensive hydrogen bond formations in which eight independent water molecules per complex pair participated. A prominent stacking interaction, characterized by a parallel alignment of both rings with a separation distance of ca. 3.4 Å, was observed between the cytosine base and the indole ring. Combining the present results with X-ray crystallographic data on the adenine- and guanine-aromatic amino acid interactions, we summarize the structural characteristics observed in the stacking interaction of the N-quarternized nucleic acid base with the aromatic amino acid and discuss their biological implications, especially in connection with the significance of N-protonation of nucleic acid base for selective recognition by protein. © 1990.