Journal article
Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes
Organic & biomolecular chemistry, Vol.10(26), pp.5077-5083
01/01/2012
DOI: 10.1039/c2ob25301a
PMID: 22627275
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.
Details
- Title: Subtitle
- Hydrogen bond-assisted macrocyclic oligocholate transporters in lipid membranes
- Creators
- Lakmini Widanapathirana - Iowa State UniversityXueshu Li - Iowa State UniversityYan Zhao - Iowa State University
- Resource Type
- Journal article
- Publication Details
- Organic & biomolecular chemistry, Vol.10(26), pp.5077-5083
- Publisher
- Royal Soc Chemistry
- DOI
- 10.1039/c2ob25301a
- PMID
- 22627275
- ISSN
- 1477-0520
- eISSN
- 1477-0539
- Number of pages
- 7
- Grant note
- DMR-1005515 / NSF; National Science Foundation (NSF)
- Language
- English
- Date published
- 01/01/2012
- Academic Unit
- Occupational and Environmental Health
- Record Identifier
- 9984303160402771
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