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Acidic Dissociation of 7 : 9-Dialkylguanines and its Possible Relation to Mutagenic Properties of Alkylating Agents

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Abstract

Watson and Crick1 proposed as a possible mechanism for mutation that changes in the tautomeric structure of a base of deoxyribonucleic acid (DNA) could induce its pairing with an anomalous base. In considering the possible correlation between the action of alkylating agents on DNA and the mutagenic activity of these agents, we mentioned in a recent report2 that it was not obvious how the initial action of alkylation of DNA, which has been shown to occur at N(7) of guanine moieties3,4, could affect base-pairing in DNA according to the Watson–Crick model. We therefore suggested that the subsequent loss of the alkylated guanine moiety from DNA (refs. 4 and 5) might be the chemical action necessary for mutation to result.

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References

  1. Watson, J. D., and Crick, F. H. C., Nature, 171, 964 (1953).

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  2. Lawley, P. D., and Brookes, P., Ann. Rep. Brit. Empire Cancer Campaign, 38, 10 (1960).

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  3. Lawley, P. D., and Wallick, C. A., Chem. and Indust., 633 (1957).

  4. Brookes, P., and Lawley, P. D., Biochem. J., 77, 478 (1960).

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  5. Lawley, P. D., Proc. Chem. Soc., 290 (1957).

  6. Brookes, P., and Lawley, P. D., J. Chem. Soc., 3923 (1961).

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LAWLEY, P., BROOKES, P. Acidic Dissociation of 7 : 9-Dialkylguanines and its Possible Relation to Mutagenic Properties of Alkylating Agents. Nature 192, 1081–1082 (1961). https://doi.org/10.1038/1921081b0

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