Ka. Werbovetz et Tl. Macdonald, ON THE MECHANISM OF ARYLAMINE-DNA ADDUCT FORMATION, Bioorganic & medicinal chemistry letters, 4(19), 1994, pp. 2323-2326
7-Methoxy-9-benzylguanine was converted to a mixture of 8-keto-9-benzy
lguanine and 8-methoxy-9-benzylguanine upon treatment with aqueous bas
e. This model system highlights the reactivity of a heteroatom-N7 guan
yl species (implicated as an intermediate in the mechanism of formatio
n of arylamine-guanine adducts) toward nucleophilic attack at C8.