Effect of chirality in gamma-PNA: PNA interaction, another piece in the picture

Molecular Assembly of Triplex of Duplexes from Homothyminyl-Homocytosinyl Cγ(S/R)-Bimodal Peptide Nucleic Acids with dA8/dG6 and the Cell Permeability of Bimodal Peptide Nucleic Acids

“…Again, the S -triplex was significantly more stable than the R -triplex by +15.2 °C. The results with triplexes are consistent with literature precedence on duplexes that Cγ­( S ) substitution stabilizes PNA:DNA duplexes better than Cγ­( R )-substitution …”

“…The high avidity of PNA for complementary DNA/RNA has been employed in various applications for DNA/RNA diagnostics and antisense therapeutics . The simplicity of the PNA structure, ease of synthesis, and its remarkable properties broaden its scope for new applications through backbone modification and conjugation with ligands that recognize cells for use as putative gene regulatory agents. , The chemical substitutions at Cα and Cγ on the aeg -PNA backbone do not significantly impede its hybridization with complementary DNA/RNA. , The introduction of cationic alkylamino, guanidino, and polyethylene glycol substituents at Cα or Cγ of aeg -PNA improved its binding to DNA and cell penetration. , One class of modifications that constrains the aeg backbone is by intraresidue cyclization to five-membered cyclopentyl, proline/pyrrolidine rings or six-membered cyclohexyl moieties, which introduces conformational pre-organization, leading to preferential hybridization with DNA or RNA. , …”

Head on Comparison of Self‐ and Nano‐Assemblies of Gamma Peptide Nucleic Acid Amphiphiles

“…Gamma modified PNAs (γ PNA) were developed by introducing a side chain at the gamma position of 2-(aminoethyl) glycine unit which induced chirality and improved binding properties contingent upon the stereochemistry. [25] MiniPEG gamma PNA ( MP γ PNA) contains a diethylene glycol unit at the gamma position which introduces a (R)-stereogenic center resulting in pre-organization of PNA into a right-handed helical conformation. [26] In addition to improving the recognition properties, γ PNAs also exhibit higher solubility, reduced self-aggregation, and superior biocompatibility in comparison to regular PNAs.…”

A minimal hybridization chain reaction (HCR) system using peptide nucleic acids

“…A g-serine modied PNA backbone was rst utilized as it improves the solubility and duplex stability compared to unmodied PNAs. 28,32,33 To evaluate the stability of the hairpins (H1 and H2) and the product of the reaction with the initiator strand (I), the PNAs were labelled with uorescein (FITC), to confer negative charges and thus allow the PNAs to migrate in polyacrylamide gel electrophoresis (PAGE). In a desirable system the initiator strand strongly hybridizes to the rst hairpin to form an I:H2 duplex, which in turn opens the second hairpin (H1) for the HCR.…”