Biotin[6]uril Esters: Chloride-Selective Transmembrane Anion Carriers Employing C-H···Anion Interactions

J Am Chem Soc. 2015 Apr 22;137(15):4948-51. doi: 10.1021/jacs.5b02306. Epub 2015 Apr 8.

Abstract

Biotin[6]uril hexaesters represent a new class of anionophores which operate solely through C-H···anion interactions. The use of soft H-bond donors favors the transport of less hydrophilic anions (e.g., Cl(-), NO3(-)) over hard, stongly hydrated anions (e.g., HCO3(-) and SO4(2-)). Especially relevant is the selectivity between chloride and bicarbonate, the major inorganic anions in biological systems.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Bridged-Ring Compounds / chemical synthesis
  • Bridged-Ring Compounds / chemistry*
  • Chlorides / chemistry*
  • Esters / chemical synthesis
  • Esters / chemistry*
  • Hydrogen Bonding
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Molecular Conformation

Substances

  • Anions
  • Bridged-Ring Compounds
  • Chlorides
  • Esters
  • Macrocyclic Compounds