Department of Materials Science & Engineering , University of California, Berkeley , Berkeley , California 94720 , United States.
The Molecular Foundry, Lawrence Berkeley National Laboratory , Berkeley , California 94720 , United States.
J Am Chem Soc. 2019 Jul 17;141(28):10953-10957. doi: 10.1021/jacs.9b03732. Epub 2019 Jul 2.
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.
虽然已经开发出许多具有疏水内腔和快速分子传输的合成纳米管，但用极性和/或响应性功能基团修饰这些通道的内部仍然具有挑战性。在水通道蛋白和 M2 通道等跨膜蛋白中，带正电荷的组氨酸残基存在于主要疏水通道中，这导致了增强的选择性和基于 pH 值的激活。在本文中，我们报告了 Bzim-CP 的合成，这是一种八肽环，其中包含苯并咪唑官能团，作为组氨酸的化学和结构模拟物。Bzim-CP 经历不同的质子化状态，形成亚纳米级纳米管，并将两个不同的可离子化官能团投射到内腔中。目前的研究为功能化亚纳米多孔通道开辟了合成可能性，为理解新的传输现象奠定了基础。
