作　　者： ; ; ; ; ; ;

机构地区： 广西师范大学

出　　处： 《有机化学》 2012年第4期742-746,共5页

摘　　要： 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. 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/Jpcis 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 3.8×104L mol-1,respectively.

关 键 词： 二茂铁 肽缀合物 合成 不饱和氨基酸 循环伏安法 荧光性质

领　　域： [理学] [理学]