Synthesis and Conformation Control of Peptide Ribonucleic Acid (PRNA) Containing 5′-Amino-5′-deoxyribopyrimidine and 5′-Amino-5′-deoxyribopurinenucleosides

Abstract

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.