Synthesis and duplex-forming ability of oligonucleotides modified with 4′-C,5′-C-methylene-bridged nucleic acid (4′,5′-BNA),Bioorganic & Medicinal Chemistry

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Synthesis and duplex-forming ability of oligonucleotides modified with 4′-C,5′-C-methylene-bridged nucleic acid (4′,5′-BNA)
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2021-08-08 , DOI: 10.1016/j.bmc.2021.116359
Takao Yamaguchi ₁ , Chika Yamamoto ₁ , Masahiko Horiba ₁ , Hiroshi Aoyama ₁ , Satoshi Obika ₂

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We describe herein the design and synthesis of 4′-C,5′-C-methylene-bridged nucleic acid (4′,5′-BNA), a novel artificial nucleic acid with the torsion angle γ in a non-canonical +ac range. The 4′,5′-BNA phosphoramidite bearing a thymine nucleobase was synthesized from a commercially available thymidine analog in 11 steps and successfully incorporated into oligonucleotides. The resulting oligonucleotides were evaluated for their duplex-forming ability toward single-stranded DNA and RNA.

中文翻译：

4'-C,5'-C-亚甲基桥接核酸（4',5'-BNA）修饰寡核苷酸的合成及双链体形成能力

我们在此描述了4'- C ,5'- C-亚甲基桥接核酸 (4',5'-BNA)的设计和合成，这是一种新型人工核酸，其扭转角为 γ 在非规范 + ac范围。带有胸腺嘧啶核碱基的 4',5'-BNA 亚磷酰胺由市售的胸苷类似物分 11 个步骤合成，并成功掺入寡核苷酸中。对所得寡核苷酸对单链 DNA 和 RNA 的双链体形成能力进行了评估。

更新日期：2021-08-12

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