双标记尿嘧啶核苷-(^(13)C,^(15)N_2)的合成研究  

Studies on the Synthesis of Uridine-(^(13)C,^(15)N_2)

作　　者：徐建飞 刘占峰 雷雯 宋明鸣 杜晓宁 XU Jianfei;LIU Zhangfeng;LEI Wen;SONG Mingming;DU Xiaoning(National isotope Engineering Technology Research Center, Shanghai Engineering Research Center of Stable Isotope, Shanghai Research Institute of Chemical Industry Company Limited, Shanghai 200062, Chin)

机构地区：[1]上海化工研究院有限公司国家同位素工程技术研究中心上海稳定性同位素工程技术研究中心,上海200062

出　　处：《化学世界》2018年第4期227-230,共4页Chemical World

基　　金：上海市科委同位素工程中心能力建设(No.15DZ2280500)资助项目

摘　　要：设计了以无水苯为溶剂,双标记尿素-(^(13)C,^(15)N_2)和丙炔酸为原料进行环化反应,粗品经脱色和重结晶后得到双标记尿嘧啶-(^(13)C,^(15)N_2)。在Ar气氛下,双标记尿嘧啶-(^(13)C,^(15)N_2)和1-乙酰氧基-2,3,5-三苯甲酰氧基-β-D-呋喃核糖反应,经处理后得到的中间体1-(2,3,5-三苯甲酰氧基-β-D-呋喃核糖基)尿嘧啶-(^(13)C,^(15)N_2)用氨水水解,即可得到双标记尿嘧啶核苷-(^(13)C,^(15)N_2)。该方法操作简单,中间体只需简单纯化,各步反应收率高,并且^(13)C、^(15)N同位素丰度不被稀释。产物经高效液相色谱法(HPLC)、MS、~1H NMR和^(13)C NMR表征,结果表明,双标记尿嘧啶核苷-(^(13)C,^(15)N_2)质量分数>98%,^(15)N同位素丰度>98%,^(13)C同位素丰度>98%。A new cyclization syntheticroutefordouble labeled uridine-（^（13）C,^15）N2）was developed usingpropiolic acid as starting materialand anhydrous benzene as solvent,and the crude product waspurified by decolorization and recrystallization for affording the desired compound.The reaction of double labeled uracil-（^（13）C,^（15）N2）and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose was conducted under to give the intermediate followed by the hydrolysis with ammonia for providing uridine-（^（13）C,^（15）N2）.This route possesses the advantages of simple operation,short process flow,high yield,and the keeping of original ^（13）C and ^（15）N labeled isotope abundance. The product was characterized by high performance liquid chromatography（HPLC）,MS,~1H NMR,and ^（13）C NMR and the results showed that the purity is higher than 98% andthe abundances of ^（13）C and ^（15）N labeled isotope areboth higher than 98%.

关 键 词：双标记 尿嘧啶 尿嘧啶核苷 

分 类 号：O621.3[理学—有机化学] R817[理学—化学]