Gelation capability of cysteine-modified cyclo(L-Lys-L-Lys)s dominated by Fmoc and Trt protecting groups

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• 作者：Huimin Geng ; Qianying Zong ; Jie You ; Lin Ye ; Aiying Zhang…
• 关键词：organogel ; cyclic dipeptide ; self ; assembly ; cysteine ; β ; turn
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：59
• 期：3
• 页码：293-302
• 全文大小：1,601 KB
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• 作者单位：Huimin Geng (1)
  Qianying Zong (1)
  Jie You (1)
  Lin Ye (1)
  Aiying Zhang (1)
  Ziqiang Shao (1)
  Zengguo Feng (1)
  
  1. School of Materials Science and Engineering, Beijing Institute of Technology, Beijing, 100081, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chinese Library of Science
  Chemistry
  
• 出版者：Science China Press, co-published with Springer
• ISSN：1869-1870

文摘

A series of symmetrical peptidomimetics (3–8) based on cysteine-modified cyclo(L-Lys-L-Lys)s were synthesized, and their gelation capability in organic solvents was dominated by fluorenylmethyloxycarbonyl (Fmoc) and triphenylmethyl (Trt) protecting groups and the exchange of thiol-to-disulfide as well. The peptidomimetics holding Trt (3 and 4) showed no gel performance, while the Fmoc groups promoted 5 and 6 to give rise to thermo-reversible organogels in a number of organic solvents. The self-assembled fibrillar networks were distinctly evidenced in the organogels by transmission electron microscopy (TEM) and scanning electron microscopy (SEM) observations. Fourier transform infrared spectroscopy (FT-IR) and fluorescence analyses revealed that the hydrogen bonding and π-π stacking play as major driving forces for the self-assembly of these organogelators. A β-turn secondary structure was deduced for the organogel of 6 by virtue of X-ray diffraction, FT-IR and circular dichroism (CD) measurements, and an interdigitated bilayer structure was also presented.