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Open Access Publications from the University of California

Organic Nanotube with Subnanometer, pH-Responsive Lumen.

  • Author(s): Darnall, Shawn M;
  • Li, Changyi;
  • Dunbar, Martha;
  • Alsina, Marco;
  • Keten, Sinan;
  • Helms, Brett A;
  • Xu, Ting
  • et al.

While many synthetic nanotubes with a hydrophobic lumen and fast molecular transport have been developed, decorating the interior of these channels with polar and/or responsive functional groups remains challenging. In transmembrane proteins like the aquaporin and M2 channels, the presence of histidine residues in a mostly hydrophobic channel has led to enhanced selectivity and pH-based activation. Herein, we report the synthesis of Bzim-CP, a cyclic octapeptide that contains a benzimidazole functionality as a chemical and structural mimic of histidine. Bzim-CP undergoes different protonation states, forms subnanometer nanotubes, and projects two different ionizable functionalities into the lumen. Present studies open up synthetic possibilities to functionalize subnanometer porous channels as a basis toward understanding new transport phenomena.

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