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Issue 7, 2018
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Lipid bilayer environments control exchange kinetics of deep cavitand hosts and enhance disfavored guest conformations

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Abstract

The effects on the molecular recognition properties of water-soluble deep cavitand hosts upon embedding them in phosphocholine lipid bilayer environments have been studied by 2D NMR experiments. By employing suitable guests containing 19F or 13C nuclei that can be encapsulated inside the host, 2D EXSY NMR experiments can be used to analyze and compare the in/out guest exchange rates in aqueous solution, isotropically tumbling micelles, or magnetically ordered bicelles. These analyses show that embedding the deep cavitands in lipid bilayers slows the guest exchange rate, due to the lipids acting as a “compression sleeve” around the host, restricting guest egress. This effect also enhances guest conformations in the host that are not observed in free solution, such as axial cyclohexane conformers and ketone hydrates.

Graphical abstract: Lipid bilayer environments control exchange kinetics of deep cavitand hosts and enhance disfavored guest conformations

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Publication details

The article was received on 04 Dec 2017, accepted on 11 Jan 2018 and first published on 11 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05155G
Citation: Chem. Sci., 2018,9, 1836-1845
  • Open access: Creative Commons BY license
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    Lipid bilayer environments control exchange kinetics of deep cavitand hosts and enhance disfavored guest conformations

    L. Perez, B. G. Caulkins, M. Mettry, L. J. Mueller and R. J. Hooley, Chem. Sci., 2018, 9, 1836
    DOI: 10.1039/C7SC05155G

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