Organic Nanotube with Subnanometer, pH-Responsive Lumen

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

doi:10.1021/jacs.9b03732

Title: Organic Nanotube with Subnanometer, pH-Responsive Lumen

Journal Article · 25 June 2019 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.9b03732 · OSTI ID:1634048

^[1]; Li, Changyi ^[2]; Dunbar, Martha ^[3]; Alsina, Marco ^[3]; Keten, Sinan ^[3];

^[2];

^[4]

Univ. of California, Berkeley, CA (United States). Dept. of Materials Science and Engineering
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry
Northwestern Univ., Evanston, IL (United States). Dept. of Civel & Environmental Engineering and Mechanical Engineering
Univ. of California, Berkeley, CA (United States). Depts. of Materials Science and Engineering & Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Molecular Foundry

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. In this paper, 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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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Gas Separations Relevant to Clean Energy Technologies (CGS); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); US Department of the Navy, Office of Naval Research (ONR)

Grant/Contract Number:: AC02-05CH11231; SC0001015; N00014-13-1-0760; CBET-1234305

OSTI ID:: 1634048

Journal Information:: Journal of the American Chemical Society, Vol. 141, Issue 28; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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