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Nucleic Acids Research, 1988, Vol. 16, No. 13 6175-6190
© 1988

Articles

A selective recognition mode of a nucleic acid base by an aromatic amino acid: L-phenylalanine-7-methylguanosine 5'-monophosphate stacking interaction

Toshimasa Ishida, Mitsunobu Doi and Masatoshi Inoue

Laboratory of Physical Chemistry, Osaka University of Pharmaceutical Sciences 2-10-65 Kawai, Matsubara, Osaka 580, Japan

Received April 7, 1988. Revised May 31, 1988. Accepted May 31, 1988.

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.


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