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Nucleic Acids Research, 2000, Vol. 28, No. 2 544-551
© 2000 Oxford University Press

Formation of 2'-deoxyoxanosine from 2'-deoxyguanosine and nitrous acid: mechanism and intermediates

Toshinori Suzuki, Hiroshi Ide1, Masaki Yamada, Nobuyuki Endo, Kenji Kanaori2, Kunihiko Tajima2, Takashi Morii and Keisuke Makino*

Institute of Advanced Energy, Kyoto University, Gokasho, Uji 611-0011, Japan, 1Department of Mathematical and Life Sciences, Graduate School of Science, Hiroshima University, Kagamiyama, Higashi-Hiroshima 739-8526, Japan and 2Department of Polymer Science and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan

The reaction mechanism for the formation of 2'-deoxy­oxanosine from 2'-deoxyguanosine by nitrous acid was explored using methyl derivatives of guanosine and an isolated intermediate of the reaction. When 1-methylguanosine was incubated with NaNO2 under acidic conditions, N5-methyloxanosine and 1-methylxanthosine were generated, whereas the same treatment of N2,N2-dimethylguanosine generated no product. In a similar experiment without NO2–, participation of a Dimroth rearrangement was ruled out. In the guanosine–HNO2 reaction system, an intermediate with a half-life of 5.6 min (pH 7.0, 20°C) was isolated and tentatively identified as a diazoate derivative of guanosine. The diazoate intermediate was converted into oxanosine and xanthosine at a molar ratio (oxanosine:xanthosine) of 0.26 at pH 7.0 and 20°C. The ratio was not affected by the incubation pH between 2 and 10, but increased linearly with temperature from 0.22 (0°C) to 0.32 (50°C). The addition of acetone also increased the ratio up to 0.85 (98% acetone). Based on these results, a con-ceivable pathway for the formation of 2'-deoxyoxanosine from 2'-deoxyguanosine by HNO2 is proposed.

* To whom correspondence should be addressed. Tel: +81 774 38 3517; Fax: +81 774 38 3524; Email: kmak@iae.kyoto-u.ac.jp


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