Reaction of cytosine with bisulfite and hydroxylamine.
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.
Oka
Yoshimi
Y
Institute of Scientific and Industrial Research and Career Design Laboratory for Women, Osaka University, Ibaraki, Osaka 567-0047, Japan.
Takei
Fumie
F
Nakatani
Kazuhiko
K
D003596:Cytosine / Q000737:chemistry*; D019811:Hydroxylamine / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D013447:Sulfites / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
C541630:5,6-dihydrouracil 6-sulfonic acid; D009838:Oligodeoxyribonucleotides; D013447:Sulfites; D013451:Sulfonic Acids; D019811:Hydroxylamine; D014498:Uracil; D003596:Cytosine; C042345:hydrogen sulfite