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

doi:10.1002/asia.201100385

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	Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
	Wang, Wei 1; Hong, Senglian 2,3; Andrew Tran 1; Jiang, Hao 1; Triano, Rebecca 1; Liu, Yi 4; Chen, Xing 2,3; Wu, Peng 1
刊名	CHEMISTRY-AN ASIAN JOURNAL
	2011-10-04
卷号	6 期号:10 页码:2796-2802
关键词	Bioconjugation Click Chemistry Copper Cycloaddition Glycoconjugates
ISSN号	1861-4728
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.
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000296273900020
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/73381]
专题	中国科学院化学研究所
通讯作者	Wu, Peng
作者单位	1.Yeshiva Univ, Dept Biochem, Albert Einstein Coll Med, Bronx, NY 10461 USA 2.Peking Univ, Beijing Natl Lab Mol Sci, Coll Chem & Mol Engn, Beijing 100871, Peoples R China 3.Peking Univ, Dept Biol Chem, Coll Chem & Mol Engn, Beijing 100871, Peoples R China 4.Univ Calif Berkeley, Lawrence Berkeley Lab, Mol Foundry, Berkeley, CA 94720 USA
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,2011,6(10):2796-2802.
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,6(10),2796-2802.
MLA	Wang, Wei,et al."Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition".CHEMISTRY-AN ASIAN JOURNAL 6.10(2011):2796-2802.