GFP生色团衍生物的合成及其荧光性能

摘要

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1 H NMR和13 C 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 synthe-sized by condensation between aromatic aldehydes and imidazolinones, which were obtained by acetyla-tion, substitution and Wittiong reaction, starting from N-methylacetamide or N-methylbenzamide.The structures were characterized by 1 H NMR and 13 C NMR.The optical study showed that the fluorescent emission wavelengths of most compounds were red-shifted compared with p-hydroxybenzylideneimidazo-linone.The emission wavelength of ( Z)-4-(2-hydroxy-5-nitrobenzylidene)-1-methyl-2-phenyl-1H-imi-dazol-5(4H)-one was 614 nm.