GFP生色团衍生物的合成及其荧光性能

Synthesis and Fluorescence Properties of the GFP Chromophores' Derivatives

以N-甲基乙酰胺或N-甲基苯甲酰胺为起始原料,与氯乙酰氯经酰化反应后,与叠氮钠经取代反应制得二酰亚胺(2);2在三苯基膦的催化下发生分子内氮杂Witting反应制得关键中间体——咪唑啉酮(3);3与芳醛在碱性条件下经缩合反应合成了8个新型的GFP生色团衍生物(5a^5h),其结构经1H NMR和13C NMR表征。对5a^5h的激发波长和发射波长进行了研究。结果表明,与对羟基苯咪唑啉酮(p-HOBDI)相比,大部分化合物的发射波长发生了比较显著的红移,其中2-羟基-5-硝基苯咪唑啉酮的发射波长达614 nm。

Eight novel analogs（ 5a ~ 5h） of fluorescent protein chromophore were designed and synthesized by condensation between aromatic aldehydes and imidazolinones,which were obtained by acetylation,substitution and Wittiong reaction,starting from N-methylacetamide or N-methylbenzamide. The structures were characterized by1 H NMR and13 C NMR. The optical study showed that the fluorescent emission wavelengths of most compounds were red-shifted compared with p-hydroxybenzylideneimidazolinone. The emission wavelength of（ Z）-4-（ 2-hydroxy-5-nitrobenzylidene）-1-methyl-2-phenyl-1H-imidazol-5（ 4H）-one was 614 nm.