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Journal of Bioactive and Compatible Polymers
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Synthesis and Conformation Control of Peptide Ribonucleic Acid (PRNA) Containing 5'-Amino-5'-deoxyribopyrimidine and 5'-Amino-5'-deoxyribopurinenucleosides

Hirofumi Sato

Department of Molecular Chemistry Osaka University 2-1 Yamada-oka, Suita 565-0871, Japan

Takehiko Wada

Department of Molecular Chemistry Osaka University 2-1 Yamada-oka, Suita 565-0871, Japan, Presto, Jst hiko{at}chem.eng.osaka-u.ac.jp

Yoshihisa Inoue

Department of Molecular Chemistry Osaka University 2-1 Yamada-oka, Suita 565-0871, Japan, Entropy Control Project ICORP, JST, 4-6-3 Kamishinden Toyonaka 565-0085, Japan

A novel nucleic acid model, a peptide ribonucleic acid (PRNA) tethering 5'-amino-5'-deoxypyrimidine ribonucleoside as a recognition site for nucleic acids, was designed and synthesized. It was demonstrated that the recognition behavior of PRNA could be controlled externally through switching the orientation of the pyrimidine nucleobase of PRNA induced by added borates. We extended this methodology of controlling the nucleobase orientation and recognition behavior of novel mono- and oligomeric PRNAs containing not only 5'-amino-5'-deoxypyrimidinenucleosides but also 5'-amino-5'-deoxypurinenucleosides. In the case of PRNA oligomer containing pyrimidine-purine mixed sequence, efficient orientation switching of nucleobases induced by added borates was also observed.

Key Words: antisense RNA • aminonucleoside • syn orientation • recognition control • external control

Journal of Bioactive and Compatible Polymers, Vol. 19, No. 2, 65-79 (2004)
DOI: 10.1177/0883911504042640
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