Article

Octafluorocalix[4]pyrrole: A Chloride/Bicarbonate Antiport Agent

School of Chemistry, University of Southampton, Southampton SO17 1BJ, United Kingdom.
Journal of the American Chemical Society (Impact Factor: 11.44). 02/2010; 132(10):3240-1. DOI: 10.1021/ja9092693
Source: PubMed

ABSTRACT meso-Octamethyloctafluorocalixpyrrole, a simple tetrapyrrolic macrocycle, has been shown to function as both a chloride/nitrate and a chloride/bicarbonate antiport agent for lipid bilayer transmembrane anion transport. This is the first example of a synthetic macrocyclic pyrrole-based receptor capable of transmembrane bicarbonate transport.

1 Bookmark
 · 
113 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: Synthetic receptors that function in water are important for the qualitative and quantitative detection of anions, which may act as pollutants in the environment or play important roles in biological processes. Neutral receptors are particularly appealing because they are often more selective than positively charged receptors; however, their affinity towards anions in pure water is only in range of 1–103 L mol−1. The anion-templated synthesis of a water-soluble bambusuril derivative is shown to be an outstanding receptor for various inorganic anions in pure water, with association constants of up to 107 L mol−1. Furthermore, the macrocycle discriminates between anions with unprecedented selectivity (up to 500 000-fold). We anticipate that the combination of remarkable affinity and selectivity of this macrocycle will enable the efficient detection and isolation of diverse anions in aqueous solutions, which is not possible with current supramolecular systems.
    Angewandte Chemie International Edition 01/2015; 54(1). DOI:10.1002/anie.201409895 · 11.34 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Preorganized aryltriazole foldamers 1 and 2 were designed and synthesized. NMR studies and X-ray analysis demonstrate that 1 adopts a crescent conformation driven by a series of continuous hydrogen bonds at the periphery of the foldamer, whereas 2 displays a coil conformation. NMR titrations reveal that the affinities of fully preorganized foldamer 1 for halogen anions are much stronger that those of partially preorganized foldamer 2. Furthermore, it is found that such full preorganization makes 1 an effective transmembrane transporter for the chloride anion across a lipid bilayer.
    Organic Letters 07/2014; 16(15). DOI:10.1021/ol501772v · 6.32 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: A new series of hydrogen bonded helical aromatic hydrazide oligomers and polymer that bear phenylalanine tripeptide chains have been designed and synthesized. It was revealed that the helical structures could insert into lipid bilayer to form unimolecular channels. The longest oligomeric and polymeric helical channels exhibited an NH4+/K+ selectivity that was higher than that of natural Gramicidin A, whereas the transport of a short helical channel for Tl+ could achieve efficiency as high as that of Gramicidin A.
    Journal of the American Chemical Society 09/2014; 136(38). DOI:10.1021/ja503376s · 11.44 Impact Factor

Full-text (2 Sources)

Download
23 Downloads
Available from
May 28, 2014