Development of artificial aromatic nucleic acid with cell membrane permeability

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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.