Oka Yoshimi, Peng Tao, Takei Fumie, Nakatani Kazuhiko
Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
Org Lett. 2009 Mar 19;11(6):1377-9. doi: 10.1021/ol900195z.
The synthesis of DNA oligomers containing N(4)-hydroxy-5,6-dihydrocytosine-6-sulfonate by using ligand-induced base flipping of cytosine followed by the simultaneous addition of bisulfite and hydroxylamine is reported. In contrast to C, the flipped-out 5-methylcytosine was selectively oxidized over thymines and cytosines in the duplex by potassium permanganate. Ligand-induced base flipping is a convenient and powerful strategy for the synthesis of modified cytosines and 5-methylcytosines related to bisulfite sequencing at the predetermined site of DNA.
报道了通过胞嘧啶的配体诱导碱基翻转，随后同时添加亚硫酸氢盐和羟胺来合成含有N(4)-羟基-5,6-二氢胞嘧啶-6-磺酸盐的DNA寡聚物。与胞嘧啶不同，双链体中翻转出的5-甲基胞嘧啶被高锰酸钾选择性地氧化，优于胸腺嘧啶和胞嘧啶。配体诱导的碱基翻转是一种方便且强大的策略，用于在DNA的预定位点合成与亚硫酸氢盐测序相关的修饰胞嘧啶和5-甲基胞嘧啶。
