Aza-Bambusurils En Route to Anion Transporters

Mandeep Singh, Ephrath Solel, Ehud Keinan, Ofer Reany

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Previous calculations of anion binding with various bambusuril analogs predicted that the replacement of oxygen by nitrogen atoms to produce semiaza-bambus[6]urils would award these new cavitands with multiple anion binding properties. This study validates the hypothesis by efficient synthesis, crystallography, thermogravimetric analysis and calorimetry. These unique host molecules are easily accessible from the corresponding semithio-bambusurils in a one-pot reaction, which converts a single anion receptor into a potential anion channel. Solid-state structures exhibit simultaneous accommodation of three anions, linearly positioned within the cavity along the main symmetry axis. The ability to hold anions at a short distance of about 4 Å is reminiscent of natural chloride channels in E. coli, which exhibit similar distances between their adjacent anion binding sites. The calculated transition-state energy for double-anion movement through the channel suggests that although these host–guest complexes are thermodynamically stable they enjoy high kinetic flexibility to render them efficient anion channels.

Original languageEnglish
Pages (from-to)8848-8854
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number26
DOIs
StatePublished - 20 Jun 2016
Externally publishedYes

Keywords

  • anion transporters
  • bambusuril
  • cavitands
  • glycoluril
  • host–guest interactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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