Electrophilic amination of guanine derivatives. Mechanism for formation of 8-aminoguanine derivatives
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説明
Abstract 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 the reaction of carcinogenic arylamines and arylhydroxylamines with cellular DNA.
収録刊行物
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- Tetrahedron
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Tetrahedron 46 1531-1540, 1990-01-01
Elsevier BV