Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction

doi:10.1016/j.carres.2012.10.001

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	Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction
	Xue, Jia-Lu 1,2; He, Xiao-Peng 1,2; Yang, Jin-Wei 1,2; Shi, De-Tai 1,2; Cheng, Chao-Ying 1,2; Xie, Juan 3; Chen, Guo-Rong 1,2; Chen, Kaixian1,2,4
刊名	CARBOHYDRATE RESEARCH
	2012-12-01
卷号	363 页码:38-42
关键词	Triazolyl bidentate glycoligand (TBG) Click chemistry Coumarin Fluorogenic chemistry Chemosensor
ISSN号	0008-6215
DOI	10.1016/j.carres.2012.10.001
文献子类	Article
英文摘要	Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.
资助项目	National Natural Science Foundation of China[21176076] ; National Natural Science Foundation of China[21202045] ; Fundamental Research Funds for the Central Universities[WK1013002] ; China Postdoctoral Science Foundation[2011M500069] ; China Postdoctoral Science Foundation[2012T50400]
WOS关键词	TERMINAL ALKYNES ; EFFICIENT SYNTHESIS ; CHEMISTRY ; SUGAR ; INHIBITORS ; LIGANDS ; SENSOR ; AZIDES ; GLYCOCLUSTERS ; DERIVATIVES
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
语种	英语
出版者	ELSEVIER SCI LTD
WOS记录号	WOS:000310924600007
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277865]
专题	药物发现与设计中心中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	He, Xiao-Peng
作者单位	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.ENS Cachan, Inst Alembert, PPSM, F-94235 Cachan, France; 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Xue, Jia-Lu,He, Xiao-Peng,Yang, Jin-Wei,et al. Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction[J]. CARBOHYDRATE RESEARCH,2012,363:38-42.
APA	Xue, Jia-Lu.,He, Xiao-Peng.,Yang, Jin-Wei.,Shi, De-Tai.,Cheng, Chao-Ying.,...&Chen, Kaixian.(2012).Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction.CARBOHYDRATE RESEARCH,363,38-42.
MLA	Xue, Jia-Lu,et al."Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction".CARBOHYDRATE RESEARCH 363(2012):38-42.