Nucleic acid secondary structures containing the double-headed nucleoside 5′(S)-C-(2-(thymin-1-yl)ethyl)thymidine
作者:Charlotte Andersen、Pawan K. Sharma、Mikkel S. Christensen、Signe I. Steffansen、Charlotte M. Madsen、Poul Nielsen
DOI:10.1039/b810930c
日期:——
Oligodeoxynucleotides containing the double-headed nucleoside 5'(S)-C-(2-(thymin-1-yl)ethyl)thymidine were prepared by standard solid phase synthesis. The synthetic building block for incorporating the double-headed moiety was prepared from thymidine, which was stereoselectively converted to a protected 5'(S)-C-hydroxyethyl derivative and used to alkylate the additional thymine by a Mitsunobu reaction
通过标准固相合成制备含有双头核苷5'(S)-C-(2-(胸苷-1-基)乙基)胸苷的寡脱氧核苷酸。由胸苷制备用于掺入双头部分的合成结构单元,将其立体选择性地转化为受保护的5'(S)-C-羟乙基衍生物,并通过Mitsunobu反应将其用于附加的胸腺嘧啶的烷基化。在不同的核酸二级结构中研究了寡脱氧核苷酸:双链体,凸出的双链体,三向连接和人工DNA拉链基序。研究了这些复合物的热稳定性,证明了将一个双头核苷部分掺入双链体或凸起的双链体中几乎均匀的热损失,可与先前报道的双头核苷5'的作用相媲美。(S)-C-(胸腺嘧啶-1-基)甲基胸苷。当掺入DNA或RNA三向连接时,附加碱基仅显示出很小的作用。各种DNA拉链排列表明,将连接子从亚甲基延伸至乙烯几乎完全消除了在(-3)拉链中观察到的亚甲基连接子的选择性小沟碱基-碱基堆积相互作用,而观察到的相互作用虽然稍小,但仍能观察到。 (-4)-拉链图案中的乙烯接头。