文献类型：期刊文献

英文题名：Creation of 3,4-bis-triazolocoumarin-sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media

作者：He, Xiao-Peng[1,2,3];Song, Zhuo[1,2,3];Wang, Zhi-Zhou[1,2,3];Shi, Xiao-Xin[1,2,3];Chen, Kaixian[1,2,3,4];Chen, Guo-Rong[1,2,3]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[4]Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

年份：2011

卷号：67

期号：19

起止页码：3343

外文期刊名：TETRAHEDRON

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000290602000005)】；

基金：This project was supported by National Natural Science Foundation of China (Grant No. 20876045), Shanghai Science and Technology Community (No. 10410702700), and the Fundamental Research Funds for the Central Universities (No. WK1013002). X.-P.H. also gratefully acknowledges the French Embassy in China for a co-tutored doctoral program.

语种：英文

外文关键词：Fluorogenic; Click chemistry; Glycosyl coumarin; Silver(I); Quenching

摘要：Fluorogenic click chemistry has recently emerged as an ingenious and powerful tool toward numerous biochemical purposes. We describe herein the use of dual click chemistry toward the fluorescence restoration of a fluorogenic coumarin on epimeric dipropargyl sugar scaffolds and their practical utility in selective metal ion detection. The dual click reactions were smoothly proceeded under microwave irradiation between silylated 3,4-di-O-propynyl gluco- or galactoside and 3-azidocoumarin, forming fluorescently reactivated bis-triazolocoumarins on sugar templates. Subsequent desilylation resulted in the OH-glycosides with desired water solubility. The following photochemical study disclosed that their fluorescence could be uniquely quenched by silver(I) in aqueous media with very minor responses to the addition of other metal ions. This research would presumably prompt the efficient creation of water soluble and potentially low toxic chemosensors via the fluorogenic dual click chemistry in using the universally existent sugars as the central scaffold. (C) 2011 Elsevier Ltd. All rights reserved.