Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.
Org Biomol Chem. 2011 Jan 7;9(1):210-8. doi: 10.1039/c0ob00248h. Epub 2010 Oct 29.
2'-O-(1-Naphthyl)uridine and 2'-O-(2-naphthyl)uridine were synthesized by a microwave-mediated reaction of 2,2'-anhydrouridine with naphthols. Using the 3'-phosphoramidite building blocks, these 2'-O-aryluridine derivatives were incorporated into 2'-O-methylated oligoribonucleotides. Incorporation of five 2'-O-(2-naphthyl)uridines into a 2'-O-methylated RNA sense strand significantly increased the thermostability of the duplex with a 2'-O-methylated RNA antisense strand. Circular dichroism spectroscopy and molecular dynamic simulation of the duplexes formed between the modified RNAs and 2'-O-methyl RNAs suggested that there are π-π interactions between two neighboring naphthyl groups in a sequence of the five consecutively modified nucleosides.
2'-O-(1-萘基)尿嘧啶核苷和 2'-O-(2-萘基)尿嘧啶核苷是通过 2,2'-脱水尿嘧啶核苷与萘酚的微波介导反应合成的。使用 3'-亚磷酰胺基构建块，将这些 2'-O-芳基尿嘧啶核苷衍生物掺入 2'-O-甲基化寡核糖核苷酸中。将五个 2'-O-(2-萘基)尿嘧啶核苷掺入 2'-O-甲基化 RNA 正义链中，显著提高了与 2'-O-甲基化 RNA 反义链形成的双链体的热稳定性。对修饰 RNA 和 2'-O-甲基 RNA 形成的双链体的圆二色性光谱和分子动力学模拟表明，在连续修饰的五个核苷酸碱基序列中，两个相邻的萘基基团之间存在 π-π 相互作用。
