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- W2085434957 abstract "The nitrenium ions 3a,b derived from hydrolysis of N-(sulfonatooxy)-N-acetyl-4-aminobiphenyl (1a) and N-(4-biphenylyl)-O-pivaloylhydroxylamine (1b) are trapped by the purine nucleosides 2‘-deoxyguanosine (dG), guanosine (G), 8-methylguanosine (8-MeG), adenosine (A), inosine (I), and xanthosine (X) with varying degrees of efficiency. Those nucleosides with a basic N-7 (pKa(N7−H+) ≥ 2.3) react with 3a,b with an apparently diffusion-limited rate constant at 20 °C of ca. 2.0 × 109 M-1 s-1, determined from the experimental trapping ratios knuc/ks and known values of ks for the two nitrenium ions. All nucleosides with a basic N-7, including 8-MeG, generate only C-8 adducts upon reaction with 3a,b. The reactions of 8-MeG with 3a,b produce metastable adducts, tentatively identified as 16a,b, that decompose over time into the stable 7,8-dihydroguanosine derivatives 8a,b. Our data, and those of other workers, are consistent with a mechanism that involves initial attack of N-7 on the nitrogen of the nitrenium ions f..." @default.
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- W2085434957 date "1997-08-01" @default.
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- W2085434957 title "Reactions of Ester Derivatives of Carcinogenic <i>N</i>-(4-Biphenylyl)hydroxylamine and the Corresponding Hydroxamic Acid with Purine Nucleosides" @default.
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- W2085434957 doi "https://doi.org/10.1021/ja970698p" @default.
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