Repositioning Chloride Transmembrane Transporters: Transport of Organic Ion Pairs

Given the biological importance of organic cations, the facilitated transport of organic ion pairs could find many applications. Calix[6]arene tris(thio)ureas, which possess a cavity that can accommodate primary ammonium ions, can not only act as carriers for Cl−/NO3− antiport but can also perform t...

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Bibliographic Details
Published in:Angewandte Chemie 2019-05, Vol.131 (21), p.6995-6999
Main Authors: Grauwels, Glenn, Valkenier, Hennie, Davis, Anthony P., Jabin, Ivan, Bartik, Kristin
Format: Article
Language:English
Subjects:
Ammonium
Antiport
Aromatic compounds
Calixarene
Cations
Chemistry
Chloride transport
Fluorescence
Fluorescence spectroscopy
Ion pairs
Ionentransport
Ions
Membranen
NMR
Nuclear magnetic resonance
Reagents
Receptors
Rezeptoren
Supramolekulare Chemie
Transport
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Summary:Given the biological importance of organic cations, the facilitated transport of organic ion pairs could find many applications. Calix[6]arene tris(thio)ureas, which possess a cavity that can accommodate primary ammonium ions, can not only act as carriers for Cl−/NO3− antiport but can also perform the cotransport of PrNH3Cl. Transport was monitored by fluorescence spectroscopy and the presence of the different species inside the vesicles was characterized by 1H and 35Cl NMR experiments involving shift reagents. The cotransport of PrNH3Cl was also observed by receptors deprived of a cavity, but the presence of the cavity conveys an advantage, as the cotransport by calix[6]arenes was observed to be more efficient than the Cl−/NO3− antiport, which is not the case with receptors without a cavity. The role played by the cavity was further highlighted by the disappearance of this advantage when using a bulky ammonium ion, which cannot be complexed within the cavity. Transporter für organische Ionenpaare: Calix[6]arentris(thio)harnstoffe mit einem Hohlraum, der primäre Ammoniumionen aufnehmen kann, agieren als Transporter für PrNH3Cl durch eine Lipiddoppelschicht sowie für den Cl−/NO3−‐Antiport. Der Vorteil der Kavität zeigt sich beim Vergleich mit Rezeptoren ohne Hohlraum, ebenso wie beim Versuch, voluminösere Alkylammoniumionen zu transportieren, die im Hohlraum nicht komplexiert werden können.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201900818