Articles

Synthesis, Structure and Properties of Ferrocene-Peptide Conjugates CH3O-Fc-NH-ΔPhe-COPh

  • Pan Chengxue ,
  • Wang Zhongchang ,
  • Su Guifa ,
  • Zong Xi ,
  • Xue Wenbin ,
  • Qin Jiangke
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  • State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004

Received date: 2011-09-26

  Revised date: 2011-11-11

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 20862003), and the Natural Science Foundation Innovative Team of Guangxi Province of China (No. 2010GXNSFF013001).

Abstract

Methyl 1'-Boc-aminoferrocene-1-carboxylate (5) was synthesized from 1,1'-ferrocenedicarboxylic acid, via esterification, partially hydrolysis, reaction with sodium azide and Curtius rearrangement. The Boc protection of 5 was removed with trifluoroacetic acid (TFA), then reacted with 4-benzylidene-2-phenyl-4H-oxazol-5-one to afford a novel ferrocene-petide conjugate CH3O-Fc-NH-ΔPhe-COPh (7) with α,β-unsaturated acid residue. The compound was characterized by IR, NMR, MS and elemental analyses. Its electrochemical behavior was tested by cyclic voltammetry (CV). The results showed that the title compound exhibits a pair of well-defined redox wave at oxidation potential (Ea) and reduction potential (Ec) of CH3O-Fc-NH-ΔPhe-COPh at 0.802 and 0.714 V, respectively, in the range of 0.4~1.1 V; and the ratio of Jpa/Jpc is 1.06. Under the simulated physiological conditions, the interaction between compound 7 and bovine serum albumin (BSA) was investigated by fluorescence spectrum. Results indicated that the combination reaction of them was a single static quenching process and with a conformational change of BSA. The number of binding site n and equilibrium (binding) constant were 0.93 and 3.8×104 L?mol-1, respectively.

Cite this article

Pan Chengxue , Wang Zhongchang , Su Guifa , Zong Xi , Xue Wenbin , Qin Jiangke . Synthesis, Structure and Properties of Ferrocene-Peptide Conjugates CH3O-Fc-NH-ΔPhe-COPh[J]. Chinese Journal of Organic Chemistry, 2012 , 32(04) : 742 -746 . DOI: 10.6023/cjoc1109263

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