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Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (10): 1492-1496. Previous Articles Next Articles
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李学强,魏传晚,刘晓芳,刘又年
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国家自然科学基金
LI Xue-Qiang, WEI Chuan-Wan, LIU Xiao-Fang, LIU You-Nian
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Fc-Gly-Lys-Leu-Val-Phe-Phe-Gly-Lys-OH (Fc-GKLVFFGK, Fc: ferrocenoyl) was synthesized from ferrocene monocarboxylic acid, Gly, Phe, Leu Val and Lys by solid-phase peptide synthesis method using O-(benzotriazol-yl)-N,N,N ,N -tetramethyluronium (HBTU)/1-hydroxybenzotrizole (HOBT) as coupling reagents. The crude peptide was purified by HPLC. The title peptide, Fc-Gly-Lys-Leu-Val-Phe-Phe- Gly-Lys-OH (Fc-GKLVFFGK), was then characterized by IR, UV, NMR and MS techniques. The voltammetric method was employed to determine the electrochemi-cal properties of the title compound. The electrochemical results showed that the title compound exhibit a pair of well-defined redox wave at oxidation potential (Ea) and reduction potential (Ec) at 0.464 and 0.396 V, respectively, in the range of 0.2~0.7 V, and the ratio of Ipa and Ipc is 1.07. The inhibitory properties of Fc-GKLVFFGK for the aggregation of β-amyloid peptide (Aβ1-42) were investigated by thiofla-vin T (ThT) fluorescence spectroscopy in vitro. The experimental results showed that the inhibitory effect of the ferrocene attached GKLVFFGK for the aggregation of Aβ1-42 is better than that of KLVFF itself. Moreover, Fc-GKLVFFGK is able to partially disaggregate performed Aβ fi-brils.
Key words: ferrocenoyl peptide, solid phase peptide synthesis, electrochemical property
LI Xue-Qiang, WEI Chuan-Wan, LIU Xiao-Fang, LIU You-Nian. Synthesis of Ferrocenoyl-peptide and Its Inhibition for β-Amyloid Peptide[J]. Chin. J. Org. Chem., 2010, 30(10): 1492-1496.
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