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Updated: Jun 20, 2026

DNA Methylation: Bisulphite Modification and Analysis
Published on: October 21, 2011
Reaction of cytosine with bisulfite and hydroxylamine
Yoshimi Oka1, Fumie Takei, Kazuhiko Nakatani
1Institute of Scientific and Industrial Research and Career Design Laboratory for Women, Osaka University, Ibaraki, Osaka 567-0047, Japan.
Abstract:
The synthesis of DNA oligomer containing N(4)-hydroxy-5,6-dihydrocytosine-6-sulfonate by the simultaneous addition of bisulfite and hydroxylamine under mild conditions is reported. To the best of our knowledge, the reaction of the oxime into the ketone, N(4)-hydroxy-5,6-dihydrocytosine-6-sulfonate into 5,6-dihydrouracil-6-sulfonate or uracil has not been reported. Moreover, this issue contains the difficulty in specific reactivity of oxime derivative from DNA bases include (5m)C toward reagent; for example, T also reacts to potassium permanganate known as a reagent for oxime into ketone. Here we examined the transformation of DNA containing N(4)-hydroxy-5,6-dihydrocytosine-6-sulfonate into 5,6-dihydrouracil 6-sulfonate and the following elimination of sulfonate.
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