Alkylation of nucleic acids and their components

In water at pH 5–6,-(N--chloroethyl-N-methylamino)propylphthalimide (I) alkylates guanosine to give 7-{-[N-methyl-N-(-phthalylimidopropyl)amino]ethyl} guanosine. The latter is converted to 7-{-[N-methyl-N-(-phthalylimidopropyl)amino] ethyl} guanine and 7-[-(N--aminopropyl-N-methylamino) ethyl]guanine. At pH 9, I and its derivatives undergo opening of the phthalimide ring to give o-carboxybenzamido derivatives. The chief transformation of I at pH 6 is self-alkylation to give quaternary ammonium bases. The pK_a and true rate constant for ionization of the chlorine of the-chloroethylamino group were determined for I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 413–418, March, 1973.See [1] for communication VI.