二茂铁-肽Fc-Gly-Pro-Arg(NO2)-OMe的合成及其与Cu(II)作用

doi:10.3866/PKU.WHXB20100827

物理化学学报 >> 2010, Vol. 26 >> Issue (09): 2381-2386.doi: 10.3866/PKU.WHXB20100827

二茂铁-肽Fc-Gly-Pro-Arg(NO₂)-OMe的合成及其与Cu(II)作用

刘晓芳, 李学强, 叶武龙, 周彬彬, 刘又年

中南大学化学化工学院, 长沙 410083

收稿日期:2010-03-09 修回日期:2010-04-18 发布日期:2010-09-02
通讯作者: 刘又年 E-mail:liuyoun@mail.csu.edu.cn
基金资助:
国家自然科学基金(20876179)资助项目

Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)

LIU Xiao-Fang, LI Xue-Qiang, YE Wu-Long, ZHOU Bin-Bin, LIU You-Nian

College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China

Received:2010-03-09 Revised:2010-04-18 Published:2010-09-02
Contact: LIU You-Nian E-mail:liuyoun@mail.csu.edu.cn
Supported by:
The project was supported by the National Natural Science Foundation of China (20876179).

摘要/Abstract

摘要：

以二茂铁甲酸、甘氨酸(H-Gly-OMe)、脯氨酸(Boc-Pro-OH)、精氨酸(H-Arg(NO₂)-OMe)等为原料, 苯并三唑-1-四甲基六磷酸酯(HBTU)和1-羟基苯并三唑(HOBT)为缩合剂, 采用液相法合成了二茂铁-肽Fc-Gly-Pro-Arg (NO₂)-OMe (简称Fc-GPR), 其总收率为48.1%. 并对目标产物进行了红外(IR)光谱、核磁共振氢谱(1H-NMR)、质谱(ESI-MS)等表征. 通过电化学方法研究了目标产物与Cu(II)之间的相互作用. 结果表明: 目标产物在溶液中的电化学行为表现为可逆氧化还原反应, 氧化和还原峰电位分别为0.624 和0.552 V(vs Ag/AgCl), 氧化和还原峰电流之比I_pa/I_pc为1.13, 电极反应过程为扩散控制. 目标产物与Cu(II)形成配位比为2:1 的配合物. Fc-GPR 与Cu(II)的电极反应过程符合电化学-化学-电化学(ECE)历程.

关键词: 二茂铁-肽, 液相合成, Gly-Pro-Arg, 电化学-化学-电化学历程, 铜离子

Abstract:

N-ferrocenoyl-labeled tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe(Fc-GPR) was synthesized from ferrocene-carboxylic acid, glycine (H-Gly-OMe), proline (Boc-Pro-OH) and arginine (H-Arg(NO₂)-OMe) by solution synthesis with a yield of 48.1%. The synthesized Fc-GPR was characterized by infrared spectroscopy (IR), proton nuclear magnetic resonance spectroscopy (¹H-NMR) and electrospray ionization mass spectroscopy (ESI-MS). The electrochemical behavior of Fc-GPR was investigated using electrochemical methods. We observed a pair of well-defined voltammetric peaks with cathodic E_pc and anodic peak potentials E_pa, at 0.552 and 0.624 V (vs Ag/AgCl), respectively. The ratio of oxidative to reductive peak current is 1.13 and the peak currents were found to be proportional to the square root of the scan rates suggesting that Fc-GPRundergoes a reversible electron transfer reaction. The molar ratio of Fc-GPR to Cu(II) was found to be 2:1 by the molar ratio method. Furthermore, the electrode reaction of Fc-GPR with Cu(II) is an electrochemical-chemical-electrochemical (ECE) process.

Key words: Ferrocene-peptide, Solution synthesis, Gly-Pro-Arg, Electrochemical-chemical-electrochemical process, Cu(II)

MSC2000:

O641

刘晓芳, 李学强, 叶武龙, 周彬彬, 刘又年. 二茂铁-肽Fc-Gly-Pro-Arg(NO₂)-OMe的合成及其与Cu(II)作用[J]. 物理化学学报, 2010, 26(09): 2381-2386.

LIU Xiao-Fang, LI Xue-Qiang, YE Wu-Long, ZHOU Bin-Bin, LIU You-Nian. Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)[J]. Acta Phys. -Chim. Sin., 2010, 26(09): 2381-2386.

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二茂铁-肽Fc-Gly-Pro-Arg(NO₂)-OMe的合成及其与Cu(II)作用

Synthesis of Ferrocenoyl-Labeled Tripeptide Fc-Gly-Pro-Arg(NO₂)-OMe and Its Interaction with Cu(II)

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