Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base,Organic & Biomolecular Chemistry

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Synthesis and thermal stabilities of oligonucleotides containing 2′-O,4′-C-methylene bridged nucleic acid with a phenoxazine base
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-14 00:00:00 , DOI: 10.1039/c7ob01874f
Yuki Kishimoto _{1,

2,

3,

4,

5} , Akane Fujii _{1,

2,

3,

4,

5} , Osamu Nakagawa _{1,

2,

3,

4,

5} , Tetsuya Nagata _{4,

5,

6,

7,

8} , Takanori Yokota _{4,

5,

6,

7,

8} , Yoshiyuki Hari _{4,

9,

10,

11} , Satoshi Obika _{1,

2,

3,

4,

5}

Affiliation

We designed and synthesized a novel artificial 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA/LNA) with a phenoxazine nucleobase and named this compound BNAP. Oligodeoxynucleotide (ODN) containing BNAP showed higher binding affinities toward complementary DNA and RNA as compared to ODNs bearing 2′,4′-BNA/LNA with 5-methylcytosine or 2′-deoxyribonucleoside with phenoxazine. Thermodynamic analysis revealed that BNAP exhibits properties associated with the phenoxazine moiety in DNA/DNA duplexes and characteristics associated with the 2′,4′-BNA/LNA moiety in DNA/RNA duplexes.

中文翻译：

含有2'- O，4'- C-亚甲基桥连的吩恶嗪碱基的寡核苷酸的合成和热稳定性

我们设计并合成了一种新型的具有苯恶嗪核碱基的人工2'- O，4'- C-亚甲基桥连核酸（2'，4'-BNA / LNA），并将其命名为化合物BNAP。与带有2'，4'-BNA / LNA和5-甲基胞嘧啶的ODN或带有2'-脱氧核糖核苷和吩恶嗪的ODN相比，包含BNAP的寡脱氧核苷酸（ODN）表现出对互补DNA和RNA更高的结合亲和力。热力学分析表明，BNAP在DNA / DNA双链体中表现出与吩恶嗪部分相关的特性，而在DNA / RNA双链体中表现出与2'，4'-BNA / LNA部分相关的特性。

更新日期：2017-09-18

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