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

• 作 者: Huimin Geng Qianying Zong Jie You Lin Ye Aiying Zhang Ziqiang Shao Zengguo Feng
• 机 构: School of Materials Science and Engineering, Beijing Institute of Technology,
• 出 处: Science China(Chemistry)
• 发表日期: 2016年03期
• 关键词: Fmoc dominated cyclo cysteine distinctly symmetrical reversible assembly assembl

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 ?-? stacking play as major driving forces for the self-assembly of these organogelators. A ?-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.

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 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. 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 analyzes revealed that the hydrogen bonding and? -? stacking play as major driving forces for the self-assembly of these organogelators. A? -turn secondary structure was deduced for the organogel of 6 by virtue of X-ray diffraction, FT-IR and circular dichroism (CD) measure ments, and an interdigitated bilayer structure was also presented.