摘要：

The effect of adding borax and boric acids on the nucleobase orientation and recognition behavior of novel mono- and oligomeric peptide ribonucleic acids (PRNAs) has been investigated. The base orientation of 5'-amino-5'-deoxyuridine and 5'-amino-5'-deoxycytidine was shown by CD and NOE difference spectral studies to switch from anti to syn in borate buffer or upon addition of borax. The origin of this phenomenon is elucidated to be the cooperative effect of the cyclic borate esterification of the sugar's cis-2',3'-diol and the hydrogen-bonding interaction between the sugar's 5'-amino proton and the base's 2-carbonyl oxygen. Because this new strategy for switching the base orientation through the addition of borate is potentially applicable to the recognition control of nucleic acids if the sugar's 5'-proton and cis-2',3'-diol remain unmodified, we synthesized a series of PRNAs, in which the 5'-amino-5'-deoxypyrimidine ribonucleoside moiety was appended to a mono- or oligo(γ-l-glutamic acid) backbone thro...

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