5-取代胞苷的合成与性质研究

Synthesis and Properties of 5-Substituted Cytidine

本研究以3-丁炔-1-醇和苄溴为原料,合成3-炔-丁基苯甲醚,通过Sonogashira反应与5-碘胞苷合成得到(4-苄氧基)丁炔基-5-胞苷,其结构经核磁共振(1 H NMR和13 C NMR)以及质谱(MS)确证。最后通过研究极性、pH值以及粘度对其光谱性质的影响,考察其是否具有成为极性、pH值以及粘度荧光探针的潜在价值。结果表明,在不同溶剂中(4-苄氧基)丁炔基-5-胞苷均有很强发射性。随着极性增加,荧光强度出现减小趋势;荧光强度随着粘度的变化而呈上升趋势;并且插入寡聚核酸中能够保持荧光性,不对周围环境产生影响。说明其该化合物在一定程度上有成为荧光探针的价值。

In this project,3-butyne-1-alcohol and benzyl bromide 3 were used as raw materials to synthesize benzyl 3-butenyl ether.Sonogashira reaction with 5-iodocytidine was used to synthesize（4-benzoxy）-butyne-5-cytidine and its structure was confirmed by 1 H NMR and 13 C-NMRs and MS.Finally,by studying the polarity and the effects of pH value and viscosity on the spectral properties,the potential value of polar pH value and viscosity fluorescence probe was investigated.The results showed that there was a strong emissivity in different solvents 5-（4-Benzyloxy）butynyl cytidine.As the polarity increased,the fluorescence intensity decreased.The fluorescence intensity increased with the change of viscosity.And the insertion of oligomeric nucleic acid could maintain fluorescence,but did not affect the surrounding environment,which indicated that the compound was valuable as a fluorescent probe to a certain extent.