Organic Nanotube with Subnanometer, pH-Responsive Lumen

Shawn M. Darnall, Changyi Li, Martha Dunbar, Marco Alsina, Sinan Keten, Brett A. Helms*, Ting Xu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)10953-10957
Number of pages5
JournalJournal of the American Chemical Society
Issue number28
StatePublished - Jun 25 2019

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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