Aza-PNA: Engineering E-Rotamer Selectivity Directed by Intramolecular H-bonding

Abstract

The replacement of α(CH 2 ) by NH in monomers of standard aeg PNA and its homologue β-ala PNA leads to respective aza-PNA monomers (1 and 2) in which the N α H can form either an 8membered H-bonded ring with folding of the backbone (DMSO and water) or a 5-membered N α H�αCO (water) to stabilize E-type rotamers. Such aza-PNA oligomers with exclusive E rotamers and intraresidue backbone H-bonding can modulate its DNA/RNA binding and assembling properties.

Recent Advancements in Development and Therapeutic Applications of Genome-Targeting Triplex-Forming Oligonucleotides and Peptide Nucleic Acids

“…Those E/Z-rotamers influenced the orientation preference of PNA in the formation of the complex. The same research group also reported aza-PNA bearing a nitrogen atom instead of a carbon atom at the α-position (Figure 9, 36) [93]. Interestingly, the aza-PNA monomer assumed the E-form via an eight-membered hydrogen-bonded ring with backbone folding.…”