Aza-PNA: Engineering E-Rotamer Selectivity Directed by Intramolecular H-bonding.
Abdul ShirajRaghunath O RamabhadranKrishna N GaneshPublished in: Organic letters (2022)
The replacement of α(CH<sub>2</sub>) by NH in monomers of standard <i>aeg</i> PNA and its homologue β-<i>ala</i> PNA leads to respective <i>aza</i>-PNA monomers (<b>1</b> and <b>2</b>) in which the N<sub>α</sub>H can form either an 8-membered H-bonded ring with folding of the backbone (DMSO and water) or a 5-membered N<sub>α</sub>H─αCO (water) to stabilize <i>E</i>-type rotamers. Such <i>aza</i>-PNA oligomers with exclusive <i>E</i> rotamers and intraresidue backbone H-bonding can modulate its DNA/RNA binding and assembling properties.