Reaction of 1-Naphthylhydroxylamine with Calf Thymus Deoxyribonucleic Acid. Isolation and Synthesis of N-(Guanin-C⁸-yl)-1-naphthylamine

Abstract

A possible activated form of 1-naphthylamine, N-hydroxy-1-naphthylamine, reacted with the C⁸-position of guanine in deoxyribonucleic acid (DNA). Hydrolysis of the modified DNA with nuclease and acid gave N-(guanin-C⁸-yl)-1-naphthylamine as a modified base. The C⁸-position of guanine seems to be a common site of attack on DNA by activated muta-carcinogenic aromatic amines.