Division of Molecular Science, Faculty of Science and Technology, Gunma University, Tenjincho 1-5-1, Kiryu, Gunma, Japan.
Bioorg Med Chem. 2013 Dec 15;21(24):8013-8. doi: 10.1016/j.bmc.2013.08.058. Epub 2013 Sep 6.
Efficient synthesis of a dithymidine dinucleotide analog bearing a diisopropylsilyl linkage instead of a phosphodiester linkage is described with respect to its incorporation into oligonucleotides. The diisopropylsilyl linkage was introduced into the oligonucleotide by preparation of the phosphoramidite derivative of a dithymidine dimer unit. The diisopropylsilyl-modified oligonucleotide exhibited hybridization behavior with both single strand and duplex DNA. The thermal stability of both the duplex and triplex showed a relative instability compared to the corresponding natural phosphodiester DNA, because of the steric hindrance of the isopropyl group on the silicon atom.
描述了一种带有二异丙基硅基连接而不是磷酸二酯键的二胸腺嘧啶二核苷酸类似物的有效合成方法,及其在寡核苷酸中的掺入。通过制备二胸腺嘧啶二聚体单元的亚磷酰胺衍生物,将二异丙基硅基连接引入到寡核苷酸中。该二异丙基硅基修饰的寡核苷酸与单链和双链 DNA 均表现出杂交行为。与相应的天然磷酸二酯 DNA 相比,双链和三链的热稳定性都表现出相对不稳定性,这是由于硅原子上异丙基的空间位阻所致。