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Self-Assembling Nanotubes Consisting of Rigid Cyclic γ-Peptides

Authors

  • Liangchun Li,

    1. Key Laboratory of Drug-Targeting of Education, Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
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  • Hongmei Zhan,

    1. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry the Chinese Academy of Sciences, Chengdu 610041, China
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  • Pengfei Duan,

    1. Institute of Chemistry, the Chinese Academy of Sciences, Beijing, 100080, China
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  • Jian Liao,

    1. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry the Chinese Academy of Sciences, Chengdu 610041, China
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  • Junming Quan,

    1. School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
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  • Yu Hu,

    1. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry the Chinese Academy of Sciences, Chengdu 610041, China
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  • Zhongzhu Chen,

    1. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry the Chinese Academy of Sciences, Chengdu 610041, China
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  • Jin Zhu,

    1. Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry the Chinese Academy of Sciences, Chengdu 610041, China
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  • Minghua Liu,

    1. Institute of Chemistry, the Chinese Academy of Sciences, Beijing, 100080, China
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  • Yun-Dong Wu,

    Corresponding author
    1. School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
    • School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
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  • Jingen Deng

    Corresponding author
    1. Key Laboratory of Drug-Targeting of Education, Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
    • Key Laboratory of Drug-Targeting of Education, Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
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Abstract

Self-assembling cyclic peptide nanotubes (SPNs) have been extensively studied due to their potential applications in biology and material sciences. Cyclic γ-peptides, which have a larger conformational space, have received less attention than the cyclic α- and β-peptides. The self-assembly of cyclic homo-γ-tetrapeptide based on cis-3-aminocyclohexanecarboxylic acid (γ-Ach) residues, which can be easily synthesized by a one-pot process is investigated. Fourier transform infrared (FTIR) and NMR analysis along with density functional theory (DFT) calculations indicate that the cyclic homo-γ-tetrapeptide, with a non-planar conformation, can self-assemble into nanotubes through hydrogen-bond-mediated parallel stacking. Atomic force microscopy (AFM) and transmission electron microscopy (TEM) experiments reveal the formation of bundles of nanotubes in CH2Cl2/hexane, but individual nanotubes and bundles of only two nanotubes are obtained in water. The integration of TEG (triethylene glycol) monomethyl ether chains and cyclopeptide backbones may allow the control of width of single nanotubes.

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