A C-nucleoside with a stable C–C glycosidic bond can be used as a building block for chemically modified oligonucleotides (ONs). In this study, two adenosine-like C-nucleosides (d^SA and d^SO2A) bearing thieno[3,2-d]pyrimidine rings were designed and synthesized. These analogues were synthesized via the Heck reaction, and their properties as monomer nucleosides were investigated. Both the d^SA and d^SO2A monomers were not recognized by adenosine deaminase (ADA). In addition, they exhibited fluorescence emissions in the UV and visible regions of d^SA and d^SO2A, respectively. Subsequently, d^SA was converted into a phosphoramidite compound and incorporated into the ONs. The synthesized d^SA-modified ONs formed a stable duplex with DNA and RNA complements comparable to natural adenosine. Furthermore, the modified ONs exhibited fluorescence emission derived from d^SA.

具有稳定 C-C 糖苷键的 C-核苷可用作化学修饰寡核苷酸 (ON) 的构建模块。在本研究中，设计并合成了两种带有噻吩并[3,2- d ]嘧啶环的腺苷样C核苷（dSA^和dSO2A ^）。这些类似物是通过 Heck 反应合成的，并研究了它们作为单体核苷的性质。dSA和 dSO2A^单体均不被腺苷脱氨酶 (ADA) 识别^。此外，它们分别在 d ^SA和 d ^SO2 A 的紫外和可见光区域表现出荧光发射。随后，d ^SA转化为亚磷酰胺化合物并掺入 ON 中。合成的 dSA^修饰的 ON 与 DNA 和 RNA 互补物形成稳定的双链体，与天然腺苷相当。此外，修饰后的 ON 表现出源自 d ^{SA 的}荧光发射。