Abstract Synthesis of selenomethylene-locked nucleic acids nucleoside bearing an adenine base (SeLNA-A) was investigated. We first examined the stereoinversion reaction at 2′-positions of a 5′,3′-O-TIPDS-protected 4′-C-(hydroxymethyl)ribosyladenine derivative to give the corresponding arabinosyladenine. After triflation, treatment of the arabinosyladenine derivative with a mixture of selenium and sodium borohydride in ethanol managed to construct the desired SeLNA skeleton. Finally, removal of TIPDS by treating with fluoride gave the SeLNA-A nucleoside. In this study, we found the heat-labile property of SeLNA-A. It is necessary to know more precise characteristics of SeLNA to achieve its oligonucleotides synthesis.

中文翻译：

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带有腺嘌呤碱基的硒亚甲基锁定核酸 (SeLNA) 核苷单元的合成

摘要 研究了带有腺嘌呤碱基的硒亚甲基锁定核酸核苷 (SeLNA-A) 的合成。我们首先检查了 5',3'-O-TIPDS 保护的 4'-C-（羟甲基）核糖腺嘌呤衍生物的 2'-位的立体反转反应，得到相应的阿拉伯糖腺嘌呤。三氟甲磺酸化后，用乙醇中的硒和硼氢化钠的混合物处理阿拉伯糖基腺嘌呤衍生物，成功构建了所需的 SeLNA 骨架。最后，通过用氟化物处理去除 TIPDS 得到 SeLNA-A 核苷。在这项研究中，我们发现了 SeLNA-A 的热不稳定特性。有必要了解SeLNA更精确的特性以实现其寡核苷酸合成。