Sulfated Ligands for the Copper(I)-Catalyzed Azide-Alkyne Cycloaddition
文献类型：期刊论文
| 作者 | Wang, Wei1; Hong, Senglian2,3; Andrew Tran1; Jiang, Hao1; Triano, Rebecca1; Liu, Yi4; Chen, Xing2,3; Wu, Peng1 |
| 刊名 | CHEMISTRY-AN ASIAN JOURNAL
 |
| 出版日期 | 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 |
| WOS记录号 | WOS:000296273900020 |
| 出版者 | WILEY-BLACKWELL |
| 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. |
入库方式： OAI收割
来源：化学研究所
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