Ferrocene - Peptide Boc-hn-fca - Gly-gly-tyr-arg-ome, The Synthesis And Electrochemical Properties,

In this thesis, several ferrocenoyl derivates were synthesized and characterized throught eight steps: (1)at room temperature, 1, 1'-diacetylferrocene (yield 78.6%) was synthesized by ferrocene and chloroacetyl chloride in dichloromethane; (2)ferrocene-1,1'-dicarboxylic acid (yield 74.5%) was synthesized by liquid bromine oxidated in 1,4-dioxan; (3)methyl-1'-carboxy-1-ferroceneacid(yield 78.0%) was synthesized by ferrocene-1,1'-dicarboxylic acid and sodium hydroxide in ethanol; (4)1'- methoxycarbonylferrocene-1-carboxylic acid (yield 77.0%) was obtained by methyl-1'-carboxy-1-ferroceneacid and quantitative sodium hydroxide in ethanol; (5)methyl-1'-azidocarbonylferrocene-1-carboxylate(yield 67.5%) was got by 1'-methoxycarbonylferrocene-1-carboxylic acid, triethylamine and ethyl chloroformate in the mix solution of water and acetone; (6)tert-butyl 1'-methoxycarbonyl-1-ferrocenecarbamate(yield 74.5%) was synthesized by methyl-1'-azidocarbonylferrocene-1-carboxylate and tert-butyl alcohol; (7)tert-Butyl 1'-carboxy-1-ferrocenecarbamate (yield 85.0%) was synthesized by tert-butyl 1'-methoxycarbonyl-1-ferrocenecarbamate and quantitative sodium hydroxide; (8)Boc-HN-Fca-Gly-Gly-Tyr-Arg-OMe (yield 83.5%) and Boc-HN-Fca-Gly-Gly-Tyr-Arg-OH(yield 80.2%)(H₂N-Gly-Gly-Tyr-Arg-OMe was synthesized by glycin, tyrosine and arginine) was synthesized through HBTU method. Boc-HN-Fca-Gly-Gly-Tyr-Arg-OMe and Boc-HN-Fca-Gly-Gly-Tyr-Arg-OH have not been reported on international. IR-Spectrum, UV-vis spectrum and ¹H NMR were taken in each step to characterize the compounds.As a result of good electrochemical properties of ferrocene, after that, a method of CV(Cyclic Voltammetry) was carried out to observe the electrochemical properties of Boc-HN-Fca-Gly-Gly-Tyr-Arg-OMe and it was proved that it was a quasireversible electrochemical process in ethanol, the oxidation potential (E_a) and reduction potential (E_c) were observed at 0.385 V and 0.346 V, The oxidation peak shifted about 41 mV to anodic and the ratio of ipa and ipc was 1.055. In this thesis, the molecules of Boc-HN-Fca-Gly-Gly-Tyr-Arg-OH were immobilized on the surface of gold electrod and a method of CV(Cyclic Voltammetry) was carried out to observe the electrochemical properties of Boc-HN-Fca-Gly-Gly-Tyr-Arg-OH in ethanol solution, the oxidation potential (E_a) and reduction potential (E_c) were observed at 0.532V and 0.453 V. The oxidation peak shifted about 79mV to anodic and the ratio of ipa and ipc was 0.928. And the papain(PAP) was detected by Boc-HN-Fca-Gly-Gly-Tyr-Arg-OMe through electrochemical methods that was fast,sensitive and simple, the oxidation potential (E_a) and reduction potential (E_c) were observed at 0.459 V and 0.271 V, The oxidation peak shifted about 188mV to anodic and the ratio of i_pa and i_pc was 1.342.