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Issue 26, 2012
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Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes

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Abstract

Three macrocyclic oligocholates containing a carboxyl group, a guanidinium ion, and a Cbz-protected amine, respectively, were studied as membrane transporters for hydrophilic molecules. To permeate glucose across lipid bilayers, the macrocycles stacked over one another to form a transmembrane nanopore, driven by a strong tendency of the water molecules in the internal cavities of the amphiphilic macrocycles to aggregate in a nonpolar environment. To transport larger guests such as carboxyfluorescein (CF), the macrocycles acted as carriers to shuttle the guest across the membrane. Hydrogen-bonds between the side chains of the macrocycles strongly affected the transport properties. Surprisingly, the carboxyl group turned out to be far more effective at assisting the aggregation of the oligocholate macrocycles in the membrane than the much stronger carboxylate–guanidinium salt bridge, likely due to competition from the phosphate groups of the lipids for the guanidinium.

Graphical abstract: Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes

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Publication details

The article was received on 10 Feb 2012, accepted on 30 Apr 2012 and first published on 01 May 2012


Article type: Paper
DOI: 10.1039/C2OB25301A
Citation: Org. Biomol. Chem., 2012,10, 5077-5083
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    Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes

    L. Widanapathirana, X. Li and Y. Zhao, Org. Biomol. Chem., 2012, 10, 5077
    DOI: 10.1039/C2OB25301A

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