Dependence of noncovalent interactions of benzene and adenine rings on distance between them in adenylyl-(5' yields N)-omega-arylalkylamines.

A series of adenylyl-(5' yields N)-omega-arylalkylamines, containing from one to six methylene groups in the amino component, was studied by methods of nuclear magnetic resonance and circular dichroism. It was shown that independently of the length of the aliphatic chain of the amine convergence of the adenine and benzene rings and a hydrophobic interaction between them occur. The plane of the benzene ring is inclined toward the adenine ring, which has an anticonformation relative to the ribose. The structure of the intramolecular complex and the energy of the interaction of the aromatic systems of the amine and nucleotide depend on the number of methylene groups in the amino component. Maximum interaction occurs in the presence of two methylene groups; weakening of the interaction occurs with an increase in the chain to four links, which does not change upon further lengthening of the chain. The conformation of adenylyl-(5' yields N)-benzylamine differs from the structure of the other compounds of the series investigated.