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

The replacement of alpha(CH2) by NH in monomers of standard aeg PNA and its homologue beta-ala PNA leads to respective aza-PNA monomers (1 and 2) in which the N alpha H can form either an 8-membered H-bonded ring with folding of the backbone (DMSO and water) or a 5-membered N alpha H-alpha CO (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.

Automated summary

Replacing alpha(CH2) with NH in monomers of standard aeg PNA and its homologue beta-ala PNA leads to aza-PNA monomers, which can form either an 8-membered H-bonded ring or a 5-membered N alpha H-alpha CO bond to stabilize E-type rotamers. These aza-PNA oligomers with exclusive E rotamers and intraresidue backbone H-bonding can modulate their DNA/RNA binding and assembling properties.