4.8 Article

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

Journal

ORGANIC LETTERS
Volume 24, Issue 40, Pages 7421-7427

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02993

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Funding

  1. IISER Pune
  2. Science and Engineering Research Board (SERB) New Delhi
  3. [EMR/2016/007601]

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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.
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.

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