Towards enzyme-like enantioselectivity in the gas phase: conformational control of selectivity in chiral macrocyclic dimers

Chem Commun (Camb). 2009 Sep 28:(36):5430-2. doi: 10.1039/b909017g. Epub 2009 Jul 31.

Abstract

Conformational factors in self-assembled chiral tetraamide macrocycles control their gas-phase enantioselectivity towards the ethyl ester of naphthylalanine to levels typical of enzymes.

MeSH terms

  • Alanine / analogs & derivatives
  • Alanine / chemistry
  • Catalysis
  • Gases / chemistry*
  • Hydrogen Bonding
  • Kinetics
  • Macrocyclic Compounds / chemistry*
  • Models, Molecular
  • Molecular Conformation*
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Stereoisomerism
  • Thermodynamics

Substances

  • Gases
  • Macrocyclic Compounds
  • Alanine