Pyrrolidinyl Peptide Nucleic Acid Research Articles

A novel pyrrolidinyl PNA showing high sequence specificity and preferential binding to DNA over RNA.

A novel conformationally constrained pyrrolidinyl peptide nucleic acid (PNA) carrying an D-aminopyrrolidine carboxylic acid (D-Apc) spacer was synthesized, and its interactions with complementary oligo- and polynucleotides were studied by UV and CD spectroscopy. The decathymine PNA formed very stable PNA-DNA complexes with poly(dA) and (dA)(10) by a sequence-specific A-T pairing. The interaction with poly(rA) gave the corresponding PNA-RNA complex with much lower stability.

Synthesis and properties of novel pyrrolidinyl PNA carrying β-amino acid spacers

Novel pyrrolidinyl peptide nucleic acids comprising alternate sequences of nucleobase-modified d-proline and β-amino acid spacers selected from l-aminopyrrolidine-2-carboxylic acid, d-aminopyrrolidine-2-carboxylic acid, (1 R,2 S)-2-aminocyclopentane carboxylic acid and β-alanine were synthesized using solid phase methodology. Gel-binding shift assay revealed that only the homothymine PNA decamer bearing d-aminopyrrolidine-2-carboxylic acid spacer binds with (dA) 10.