Oka Yoshimi, Takei Fumie, Nakatani Kazuhiko
Institute of Scientific and Industrial Research and Career Design Laboratory for Women, Osaka University, Ibaraki, Osaka 567-0047, Japan.
Nucleic Acids Symp Ser (Oxf). 2009(53):215-6. doi: 10.1093/nass/nrp108.
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.
报道了在温和条件下通过同时添加亚硫酸氢盐和羟胺合成含N(4)-羟基-5,6-二氢胞嘧啶-6-磺酸盐的DNA寡聚物。据我们所知，肟转化为酮、N(4)-羟基-5,6-二氢胞嘧啶-6-磺酸盐转化为5,6-二氢尿嘧啶-6-磺酸盐或尿嘧啶的反应尚未见报道。此外，这个问题还包括DNA碱基中肟衍生物（包括(5m)C）对试剂的特异性反应的困难；例如，胸腺嘧啶（T）也会与已知用于肟转化为酮的试剂高锰酸钾发生反应。在这里，我们研究了含N(4)-羟基-5,6-二氢胞嘧啶-6-磺酸盐的DNA向5,6-二氢尿嘧啶6-磺酸盐的转化以及随后磺酸盐的消除。
