Synthesis of selenomethylene-locked nucleic acids (SeLNA) nucleoside unit bearing an adenine base
Synthesis of selenomethylene-locked nucleic acids (SeLNA) nucleoside unit bearing an adenine base
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DOI：
10.1080/15257770.2019.1675169
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发表时间：
2020-02
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影响因子：
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通讯作者：
Yoshihiro Moai;H. Hiroaki;Satoshi Obika;T. Kodama
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文献类型：
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作者：
Yoshihiro Moai;H. Hiroaki;Satoshi Obika;T. Kodama
摘要研究了含腺嘌呤碱基的亚硒亚甲基锁定核酸(SELNA-A)的合成。我们首先研究了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，得到了相应的阿拉伯糖腺嘌呤。在摩擦后，用硒和硼氢化钠在乙醇中的混合物处理阿拉伯糖腺嘌呤衍生物，成功地构建了所需的Selna骨架。最后，用氟化物去除TIPDS得到Selna-A核苷。在本研究中，我们发现了Selna-A的热不稳定性。为了实现SELNA的寡核苷酸合成，有必要更准确地了解SELNA的特性。
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.