Transmembrane anion transport mediated by halogen-bond donors

Andreas Vargas Jentzsch, Daniel Emery, Jiri Mareda, Susanta K. Nayak, Pierangelo Metrangolo, Giuseppe Resnati, Naomi Sakai and Stefan Matile ()
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Andreas Vargas Jentzsch: University of Geneva
Daniel Emery: University of Geneva
Jiri Mareda: University of Geneva
Susanta K. Nayak: NFMLab, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano and Center for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Politecnico di Milano
Pierangelo Metrangolo: NFMLab, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano and Center for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Politecnico di Milano
Giuseppe Resnati: NFMLab, Materials and Chemical Engineering Giulio Natta, Politecnico di Milano and Center for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Politecnico di Milano
Naomi Sakai: University of Geneva
Stefan Matile: University of Geneva

Nature Communications, 2012, vol. 3, issue 1, 1-8

Abstract: Abstract In biology and chemistry, the transport of anions across lipid bilayer membranes is usually achieved by sophisticated supramolecular architectures. Significant size reduction of transporters is hampered by the intrinsically hydrophilic nature of typical anion-binding functionalities, hydrogen-bond donors or cations. To maximize the atom efficiency of anion transport, the hydrophobic nature, directionality, and strength of halogen bonds seem promising. Unlike the ubiquitous, structurally similar hydrogen bonds, halogen bonds have not been explored for anion transport. Here we report that transport across lipid bilayers can be achieved with small perfluorinated molecules that are equipped with strong halogen-bond donors. Transport is observed with trifluoroiodomethane (boiling point=−22 °C); that is, it acts as a 'single-carbon' transporter. Contrary to the destructive action of small-molecule detergents, transport with halogen bonds is leakage-free, cooperative, non-ohmic and highly selective, with anion/cation permeability ratios

Date: 2012
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DOI: 10.1038/ncomms1902

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