Tetrahedron p. 1531 - 1540 (1990)
Update date:2022-09-26
Topics:
Kohda, Kohfuku
Baba, Kunihisa
Kawazoe, Yutaka
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.
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