Iwase Reiko, Toyama Takaaki
Department of Biosciences, Teikyo University of Science and Technology, 2525 Yatsusawa, Uenohara, Yamanashi 409-0193, Japan.
Nucleic Acids Symp Ser (Oxf). 2007(51):135-6. doi: 10.1093/nass/nrm068.
To construct modified RNA that form A-type duplex with photo-irradiation, a photocleavable a-methyl-2-nitropiperonyl (MeNP) group was introduced at O(6) position of guanosine. A guanosine phosphoramidite derivative containing the MeNP group was synthesized via regioselective 2'-O-protection of 3',5'-O-di(t-butyl)silanediylguanosine with TBDMS group. The MeNP group was found to be stable under conditions of solid-phase synthesis of RNA. The MeNP group was also found to be removable by UV irradiation at wavelength of 365 nm for 10 min.
为构建经光照射形成 A 型双链体的修饰 RNA，在鸟苷的 O(6) 位引入了可光裂解的α-甲基-2-硝基哌啶基（MeNP）基团。通过用叔丁基二甲基硅烷基（TBDMS）基团对 3',5'-O-二（叔丁基）硅烷基鸟苷进行区域选择性 2'-O-保护，合成了含有 MeNP 基团的鸟苷亚磷酰胺衍生物。发现 MeNP 基团在 RNA 的固相合成条件下是稳定的。还发现 MeNP 基团可通过 365 nm 波长的紫外线照射 10 分钟去除。
