Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition

doi:10.1002/asia.201100385

CORC > 北京大学 > 化学与分子工程学院

	Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
	Wang, Wei ; Hong, Senglian ; Andrew Tran ; Jiang, Hao ; Triano, Rebecca ; Liu, Yi ; Chen, Xing ; Wu, Peng
刊名	chemistry an asian journal
	2011
关键词	bioconjugation click chemistry copper cycloaddition glycoconjugates CLICK CHEMISTRY IN-VIVO ESCHERICHIA-COLI TERMINAL ALKYNES FUNCTIONALITY OPTIMIZATION PROTEINS GLYCANS SUGARS ACIDS
DOI	10.1002/asia.201100385
英文摘要	The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), the prototypical reaction of click chemistry, is accelerated by tris(triazolylmethyl) amine-based ligands. Herein, we compare two new ligands in this family-3-[4-({bis[(1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl]amino}methyl)-1H-1,2,3-triazol-1-yl] propanol (BTTP) and the corresponding sulfated ligand 3-[4-({bis[(1-tert-butyl-1H-1,2,3-triazol-4-yl)methyl] amino}methyl)-1H-1,2,3- triazol-1-yl]propyl hydrogen sulfate (BTTPS)-for three bioconjugation applications: 1) labeling of alkyne-tagged glycoproteins in crude cell lysates, 2) labeling of alkyne- or azide-tagged glycoproteins on the surface of live mammalian cells, and 3) labeling of azides in surface proteins of live Escherichia coli. Although BTTPS exhibits faster kinetics than BTTP in accelerating the CuAAC reaction in in vitro kinetic measurements, its labeling efficiency is slightly lower than BTTP in modifying biomolecules with a significant amount of negative charges due to electrostatic repulsion. Nevertheless, the negative charge conferred by the sulfate at physiological conditions significantly reduced the cellular internalization of the coordinated copper(I), thus making BTTPS-Cu(1) a better choice for live-cell labeling.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000296273900020&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Chemistry, Multidisciplinary; SCI(E); EI; 33; ARTICLE; 10,SI; 2796-2802; 6
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/237815]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Wang, Wei,Hong, Senglian,Andrew Tran,et al. Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition[J]. chemistry an asian journal,2011.
APA	Wang, Wei.,Hong, Senglian.,Andrew Tran.,Jiang, Hao.,Triano, Rebecca.,...&Wu, Peng.(2011).Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition.chemistry an asian journal.
MLA	Wang, Wei,et al."Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition".chemistry an asian journal (2011).