ELECTROPHILIC AMINATION OF GUANINE DERIVATIVES. MECHANISM FOR FORMATION OF 8-AMINOGUANINE DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)81962-1

A study of the mechanism of 8-aminoguanosine formation in the reaction of guanosine with hydroxylamine-O-sulfonic acid (HAOS) revealed that the reaction proceeds in three steps; 1) electrophilic N-7 amination by HAOS, 2) nucleophilic C-8 hydroxyamination by NH2OH accompanied by elimination of the N-7 amino group and by aromatization, and finally 3) the reduction of the C-8 hydroxyamino group by NH2OH to give 8-aminoguanosine.The significance of formation of the 7-aminoguanosine intermediate is discussed briefly in relation to thr reaction of carcinogenic arylamines and arylhydroxylamines with cellular DNA.