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

作　　者：Huimin Geng Qianying Zong Jie You Lin Ye Aiying Zhang Ziqiang Shao Zengguo Feng 

机构地区：[1]School of Materials Science and Engineering, Beijing Institute of Technology

出　　处：《Science China Chemistry》2016年第3期293-302,共10页中国科学（化学英文版）

基　　金：the National Natural Science Foundation of China (21174018)

摘　　要：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 micros- copy （TEM） and scanning electron microscopy （SEM） observations. Fourier transform infrared spectroscopy （FT-IR） and fluorescence analyses revealed that the hydrogen bonding and ^-rt stacking play as major driving forces for the self-assembly of these organogelators. A 13-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(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.

关 键 词：ORGANOGEL cyclic dipeptide SELF-ASSEMBLY CYSTEINE β-turn 

分 类 号：O621.3[理学—有机化学] TS254.1[理学—化学]