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以二茂铁二甲酸为原料,经酯化、部分水解、与叠氮化钠反应、在叔丁醇中发生Curtius重排得到1’-甲酸甲酯-1-叔丁氧胺基二茂铁(5),5经三氟乙酸脱保护、与(Z)-2-苯基-4-苯甲基噁唑-5-酮反应,合成了含α,β-不饱和氨基酸残基的二茂铁-肽缀合物CH3O-Fc-NH-ΔPhe-COPh(7)(ΔPhe为α,β-不饱和苯丙氨酸).用红外、核磁、质谱和元素分析对其结构进行鉴定和表征.用循环伏安(CV)法对产物的电化学性能进行研究,结果表明化合物7的氧化峰和还原峰的电位分别为0.802和0.714 V,峰电位之差ΔEp为88 mV,峰电流密度之比Jpa/Jpc为1.06.用荧光光谱研究了近生理条件下化合物7与牛血清白蛋白(BSA)的相互作用,结果表明化合物7与BSA间的相互作用为静态猝灭过程,反应结合位点数为0.93,结合常数为3.8×104L mol-1.
To ferrocene dicarboxylic acid as raw material, the esterification, partial hydrolysis, and sodium azide reaction, in the tert-butanol Curtius rearrangement to give methyl 1 ’- tert-butoxyamine ferrocene (5), 5 were deprotected with trifluoroacetic acid and reacted with (Z) -2-phenyl-4-phenylmethyloxazol-5-one to synthesize a dimer containing α, β-unsaturated amino acid residues The structure of iron-peptide conjugate CH3O-Fc-NH-ΔPhe-COPh (7) (ΔPhe is α, β-unsaturated phenylalanine) was identified and characterized by IR, NMR, MS and elemental analysis. The electrochemical performance of the product was investigated by cyclic voltammetry (CV). The results showed that the potentials of the oxidation peak and the reduction peak of compound 7 were 0.802 and 0.714 V, respectively. The difference of peak potentials ΔEp was 88 mV. The peak current density ratio Jpa / Jpc was 1.06. The interaction between compound 7 and bovine serum albumin (BSA) under near physiological conditions was studied by fluorescence spectroscopy. The results showed that the interaction between compound 7 and BSA was static quenching and the number of binding sites was 0.93 with a binding constant of 3.8 × 104 L mol-1.