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Locking Interconversion of Aromatic Oligoamide Foldamers by Intramolecular Side-chain Crosslinking: toward Absolute Control of Helicity in Synthetic Aromatic Foldamers.

Lu ZhengChengyuan YuYulin ZhanXuebin DengYing WangHua Jiang
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
A series of foldamers of 8-amino-2-quinoline carboxylic acid were stapled by intramolecular ring-closing olefin metathesis to generate the constrained aromatic foldamers with varying lengths of hydrocarbon side-chains. Investigations clearly revealed that the side-chain crosslinkers are capable of completely locking the interconversions of the stapled aromatic foldamers over a wide range of temperatures in CDCl3 , even in C2 D2 Cl4 . Hence, the stapled foldamers with the short hydrocarbon crosslinker can be easily separated by silica-gel chromatography to generate foldamers with stable, absolute one-handed helicity. But the stapled foldamer with the longer crosslinker is inseparable even by chiral HPLC presumably due to the fortuitous identical polarity of the diastereomer.
Keyphrases
  • amino acid
  • mass spectrometry
  • ms ms
  • high performance liquid chromatography
  • simultaneous determination
  • single cell
  • molecular docking
  • high resolution