Genetically Encoded Copper-Free Click Chemistry

被引:246
作者
Plass, Tilman [1 ,2 ]
Milles, Sigrid [1 ,2 ]
Koehler, Christine [1 ,2 ]
Schultz, Carsten [1 ,2 ]
Lemke, Edward A. [1 ,2 ]
机构
[1] EMBL, Struct & Computat Biol Unit, D-69117 Heidelberg, Germany
[2] EMBL, Cell Biol & Biophys Unit, D-69117 Heidelberg, Germany
关键词
amino acids; click chemistry; gene expression; proteins; strained molecules; FLUORESCENT AMINO-ACID; LIVING CELLS; LIVE CELLS; RECOMBINANT PROTEINS; MAMMALIAN-CELLS; CYCLOADDITION; AZIDE; CODE; LYSINE;
D O I
10.1002/anie.201008178
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A bright click of life: Strained alkynes are genetically encoded into E. coli by use of an engineered pyrrolysine amber suppressor tRNA/synthetase pair from Methanosarcina mazei. As a result cyclooctynyl lysine derivatives were incorporated site-specifically in proteins allowing efficient labeling with fluorogenic azide-bearing dyes by means of a click reaction under physiological conditions in vitro and in vivo (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3878 / 3881
页数:4
相关论文
共 50 条
[21]   Renewable polymers from lignin via copper-free thermal click chemistry [J].
Han, Yanming ;
Yuan, Liang ;
Li, Gaiyun ;
Huang, Luohua ;
Qin, Tefu ;
Chu, Fuxiang ;
Tang, Chuanbing .
POLYMER, 2016, 83 :92-100
[22]   Cooperative capture synthesis: yet another playground for copper-free click chemistry [J].
Hou, Xisen ;
Ke, Chenfeng ;
Stoddart, J. Fraser .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (14) :3766-3780
[23]   A Genetically Encoded Picolyl Azide for Improved Live Cell Copper Click Labeling [J].
Meineke, Birthe ;
Heimgartner, Johannes ;
Craig, Alexander J. ;
Landreh, Michael ;
Moodie, Lindon W. K. ;
Elsasser, Simon J. .
FRONTIERS IN CHEMISTRY, 2021, 9
[24]   Oligonucleotide Tagging for Copper-Free Click Conjugation [J].
Jawalekar, Anup M. ;
Malik, Sudip ;
Verkade, Jorge M. M. ;
Gibson, Brian ;
Barta, Nancy S. ;
Hodges, John C. ;
Rowan, Alan ;
van Delft, Floris L. .
MOLECULES, 2013, 18 (07) :7346-7363
[25]   Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions [J].
Knight, James C. ;
Richter, Susan ;
Wuest, Melinda ;
Way, Jenilee D. ;
Wuest, Frank .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (23) :3817-3825
[26]   Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry [J].
Ramos-Soriano, Javier ;
Reina, Jose J. ;
Perez-Sanchez, Alfonso ;
Illescas, Beatriz M. ;
Rojo, Javier ;
Martin, Nazario .
CHEMICAL COMMUNICATIONS, 2016, 52 (69) :10544-10546
[27]   Copper-Free Click Chemistry: Applications in Drug Delivery, Cell Tracking, and Tissue Engineering [J].
Yoon, Hong Yeol ;
Lee, Donghyun ;
Lim, Dong-Kwon ;
Koo, Heebeom ;
Kim, Kwangmeyung .
ADVANCED MATERIALS, 2022, 34 (10)
[28]   Designed Multifunctional Spider Silk Enabled by Genetically Encoded Click Chemistry [J].
Jiang, Bojing ;
Tan, Sin Yen ;
Fang, Shiyu ;
Feng, Xiaohan ;
Park, Byung Min ;
Fok, Hong Kiu Francis ;
Yang, Zhongguang ;
Wang, Ri ;
Kou, Songzi ;
Wu, Angela Ruohao ;
Sun, Fei .
ADVANCED FUNCTIONAL MATERIALS, 2023, 33 (43)
[29]   Copper-free click chemistry on polymersomes: pre- vs. post-self-assembly functionalisation [J].
Meeuwissen, Silvie A. ;
Debets, Marjoke F. ;
van Hest, Jan C. M. .
POLYMER CHEMISTRY, 2012, 3 (07) :1783-1795
[30]   A novel dibenzoazacyclooctyne precursor in regioselective copper-free click chemistry. An innovative 3-step synthesis [J].
Starke, Frank ;
Walther, Martin ;
Pietzsch, Hans-Juergen .
ARKIVOC, 2010, :350-359