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Chemical Degradation of DMA oxidized by Permanganate

Abstract

WHEN DNA is treated with potassium permanganate at 37° C and pH 9 for 19 h, the thymine, cytosine and guanine residues are oxidized, but the adenine residues are unaffected1,2. The product (ODNA) is obtained in a high yield as a polymer in which there has been little degradation of the phosphodiester backbone of the DNA. Analytical data and the results of experiments on model compounds2–5 indicated that the thymine, cytosine and guanine residues had been oxidized to ureido residues. In view of the apparent lability of ureido sugars to alkali6,7 it seemed that the ODNA should be degraded by alkali to give oligonucleotides containing adenine. Previous work in which ODNA was degraded with alkali or with hydrazine followed by alkali seemed to support this, and from these results values for the distribution of adenine in DNA from a number of sources were obtained8,9. Reinvestigation of these reactions, and examination of other reactions of ODNA, however, have shown that the structure given before and the results quoted for the adenine distributions of the various samples of DNA were not correct.

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DARBY, G., JONES, A., TITTENSOR, J. et al. Chemical Degradation of DMA oxidized by Permanganate. Nature 216, 793–794 (1967). https://doi.org/10.1038/216793a0

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