Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (04): 742-746.DOI: 10.6023/cjoc1109263 Previous Articles     Next Articles

Articles

二茂铁-肽缀合物CH3O-Fc-NH-ΔPhe-COPh 的合成及性质研究

潘成学, 王忠长, 苏桂发, 宗玺, 薛文彬, 覃江克   

  1. 广西师范大学化学化工学院 药用资源化学与药物分子工程国家重点实验室培育基地 桂林 541004
  • 收稿日期:2011-09-26 修回日期:2011-11-11 发布日期:2012-04-24
  • 通讯作者: 苏桂发 E-mail:edward_su75@163.com
  • 基金资助:

    国家自然科学基金(No. 20862003)、广西自然科学基金创新团队(No. 2010GXNSFF013001)资助项目.

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   

  1. 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:2011-09-26 Revised:2011-11-11 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).

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.

Key words: ferrocene peptides, synthesis, α,β-unsaturated acids, cyclic voltammetry, fluorescence spectrum