Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (09): 2381-2386.doi: 10.3866/PKU.WHXB20100827

• ELECTROCHEMISTRY • Previous Articles     Next Articles

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   

  1. 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).

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 Epc and anodic peak potentials Epa, 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