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Novel Cyclopeptide Bolaamphiphile for Constructing Supramolecular Nanotubes
Author(s) -
Qin Siyong,
Wang Qingrong,
Pei Yi,
Peng Mengyun,
Zhuo Renxi,
Zhang Xianzheng
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300743
Subject(s) - chemistry , supramolecular chemistry , circular dichroism , hydrogen bond , alkyl , amphiphile , linker , fourier transform infrared spectroscopy , molecule , polymer chemistry , combinatorial chemistry , stereochemistry , organic chemistry , copolymer , polymer , chemical engineering , computer science , engineering , operating system
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.