Login / Signup

Controlling Helix Sense at N- and C-Termini in Quinoline Oligoamide Foldamers by β-Pinene-Derived Pyridyl Moieties.

Lu ZhengYulin ZhanChengyuan YuFu HuangYing WangHua Jiang
Published in: Organic letters (2017)
A series of quinoline oligoamide foldamers bearing a β-pinene-derived pyridyl group at the N-terminus or the C-terminus were synthesized, and the efficiencies of chiral inductions have been evaluated by 1H NMR and CD spectra. The chiral inductions were quantitative when chiral pyridyl acid was appended at the N-terminus, but were inferior when chiral pyridyl amine was appended at the C-terminus. Unexpectedly, N-oxidation on the pyridine ring at the C-terminus does not notably enhance the chiral induction efficiency in spite of the presence of three-center hydrogen bonds.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • high resolution
  • mass spectrometry
  • molecular docking
  • magnetic resonance
  • hydrogen peroxide
  • nitric oxide
  • molecular dynamics simulations
  • solid state
  • nk cells