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

The replacement of α­(CH2) 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 NαH can form either an 8-membered H-bonded ring with folding of the backbone (DMSO and water) or a 5-membered NαHαCO (water) to stabilize E-type r...

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Bibliographic Details
Published in:Organic letters 2022-10, Vol.24 (40), p.7421-7427
Main Authors: Shiraj, Abdul, Ramabhadran, Raghunath O., Ganesh, Krishna N.
Format: Article
Language:English
Subjects:
Dimethyl Sulfoxide
DNA - chemistry
Peptide Nucleic Acids - chemistry
RNA - chemistry
Water
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Summary:The replacement of α­(CH2) 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 NαH can form either an 8-membered H-bonded ring with folding of the backbone (DMSO and water) or a 5-membered NαH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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02993