Development of artificial aromatic nucleic acid with cell membrane permeability

本研究的目的是开发一种具有细胞膜通透性的人造芳香族核酸，它包含一个苯环而不是一个核糖环。(S)-扁桃酸为起始原料。经酯化、碘化、还原、硅烷化等反应制得硼酸衍生物。在铜(II)存在下，它与腺嘌呤或胞嘧啶发生偶联反应，以较高的产率生成腺嘌呤和胞嘧啶类似物。结果表明，类似物降低了DNA/DNA和DNA/RNA双链的热稳定性，但具有较高的碱基分辨能力。

The purpose of this study is development of artificial aromatic nucleic acid with cell membrane permeability which involves a benzene ring instead of a ribose ring. (S)-mandelic acid was used as a starting material. After esterification, iodization, reduction, and silylation, it was converted to a boronic acid derivative. Coupling reaction of it with an adenine or cytosine in the presence of cupper (II) produced adenine and cytosine analogs in good yields. It was found that the analogs reduced thermal stabilities of DNA/DNA and DNA/RNA duplexes, but the analogs possessed high base discrimination abilities.