Novel Cyclopeptide Bolaamphiphile for Constructing Supramolecular Nanotubes

Authors

  • Siyong Qin,

    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
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  • Qingrong Wang,

    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
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  • Yi Pei,

    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
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  • Mengyun Peng,

    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
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  • Renxi Zhuo,

    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
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  • Xianzheng Zhang

    Corresponding author
    1. Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China
    • Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan, Hubei 430072, China

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Abstract

A novel dicyclopeptide-based bolaamphiphile was synthesized. The hydrophilic cyclopeptide fragments were linked to an alkyl chain 1,6-bis(maleimido)hexane, which acted as a hydrophobic spacer. The transmission electron microscopy (TEM) observation indicated that the cyclopeptide bolaamphiphile (CPB) self-assembled into the nanotubes with a thickness of about 3 nm. Based on the optimized molecular conformation obtained via MM2 method, the length of CPB was demonstrated to be around 4 nm, implying that the nanotubes were single-walled. Fourier transform infrared spectroscopy (FT-IR) and circular dichroism (CD) analysis showed that the cyclopeptides in CPB mainly acted as the hydrophilic headgroups, rather than providing the well-ordered hydrogen bonding interaction responsible for β-sheet conformation. To investigate the special self-assembly behavior of CPB, the single cyclopeptide (CP) without the connection of the linker was synthesized. Further investigation indicated that the CP molecules can not form tubular structures but nanofibers.

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