Synthesis of new building blocks for peptide nucleic acids containing monomers with variations in the backbone

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

“…For instance, hetero-oligomeric PNAs composed of normal aminoethylglycine and aminoproline building blocks were assembled using the Boc strategy. [51,74] This is not the case, however, for PNA derivatives that deviate strongly from the basic aminoethylglycine structure, such as the PHONAs where special synthetic methods had to be developed. [39,75,76] …”

Hybridization Studies with Chiral Peptide Nucleic Acids

“…Guided by molecular modeling we are now exploring the effect of alternative spacer groups on thermal stability. 8 -OH (28). They reported that no hybridization was observed with the complementary oligodeoxynucleotides.…”

Structural Preorganization of Peptide Nucleic Acids: Chiral Cationic Analogues with Five- or Six-Membered Ring Structures

“…A backbone combining aegPNA alternating with -trans-4-aminoprolyl PNA was later shown to bind to the target sequences with higher affinity than the pure aegPNA oligomers. [32] Efforts directed towards releasing the structural strain in aminoprolyl PNA resulted in the synthesis of prolyl carbamate nucleic acids in which the backbone amide bond was replaced by a carbamate linkage, extended by two additional atoms (Figure 9a) [33] in comparison to the unmodified aegPNA oligomers. Thymine or mixed pyrimidine oligomers of -cis-prolyl carbamate nucleic acids were not attuned for binding with the target DNA.…”

“…The sequences with aegPNA alternating with the proline-glycine PNA unit showed reduced binding to the target sequences, unlike the 4-aminoproline PNA. [32] Figure 10. Prolylglycyl PNA with a αЈЈ-βЈ-methylene bridge…”