Amino Acids for Diels-Alder Reactions in Living Cells

被引：272
|
作者：
Plass, Tilman [1 ]
Milles, Sigrid [1 ]
Koehler, Christine [1 ]
Szymanski, Jedrzej [1 ]
Mueller, Rainer [1 ]
Wiessler, Manfred [2 ]
Schultz, Carsten [1 ]
Lemke, Edward A. [1 ]
机构：
[1] EMBL, Struct & Computat Biol Unit, D-69117 Heidelberg, Germany
[2] DKFZ, D-69120 Heidelberg, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 17期
关键词：
amber suppression; click chemistry; Diels-Alder reactions; protein engineering; unnatural amino acids; RECOMBINANT PROTEINS; CLICK CHEMISTRY; LIGATION; ALKYNE; DNA; CYCLOADDITIONS; STRATEGIES; AZIDES;
D O I：
10.1002/anie.201108231
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Under tension: A set of genetically encoded unnatural amino acids can be used for biocompatible site-specific labeling of proteins with fluorogenic dyes. The new compounds have norbornene and trans-cyclooctene units that react with tetrazine derivatives in an inverse-electron-demand Diels-Alder cycloaddition (left in picture). The technique offers fast labeling that is orthogonal to labeling through azide-cyclooctyne click reaction (right). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：4166 / 4170
页数：5
相关论文
共 50 条
  • [31] Dienophilic reactivity of perfluoroalkenyl ketones in Diels-Alder reactions
    Chanteau, F
    Essers, M
    Plantier-Royon, R
    Haufe, G
    Portella, C
    TETRAHEDRON LETTERS, 2002, 43 (09) : 1677 - 1680
  • [32] Cope rearrangements versus retro Diels-Alder reactions
    Beck, K
    Hoffman, P
    Hunig, S
    CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) : 1588 - 1599
  • [33] Regioselective Diels-Alder reactions of 3-indolylquinones
    Alonso, MA
    López-Alvarado, P
    Avendaño, C
    Menéndez, JC
    TETRAHEDRON, 2003, 59 (16) : 2821 - 2830
  • [34] Radical cation Diels-Alder reactions of arylidene cycloalkanes
    Nakayama, Kaii
    Kamiya, Hidehiro
    Okada, Yohei
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1100 - 1106
  • [35] Diastereoselective Diels-Alder reactions. The role of the catalyst
    Huang, YF
    Sonnet, PE
    Carroll, PJ
    Dalton, DR
    TETRAHEDRON LETTERS, 2000, 41 (15) : 2519 - 2522
  • [36] An approach to the synthesis of furanoheliangolides through Diels-Alder reactions
    Constantino, Mauricio Gomes
    Aragao, Valquiria
    da Silva, Gil Valdo Jose
    TETRAHEDRON LETTERS, 2008, 49 (08) : 1393 - 1395
  • [37] A Brief Review on Recent Developments in Diels-alder Reactions
    Chaudhary, Manish
    Shaik, Shareef
    Magan, Muskan
    Hudda, Sharwan
    Gupta, Mukta
    Singh, Gurvinder
    Wadhwa, Pankaj
    CURRENT ORGANIC SYNTHESIS, 2025, 22 (01) : 2 - 23
  • [38] Artificial metalloenzymes as catalysts in stereoselective diels-alder reactions
    Reetz, Manfred T.
    CHEMICAL RECORD, 2012, 12 (04) : 391 - 406
  • [39] Performance of ab initio and DFT methods in modeling Diels-Alder reactions
    Gayatri, Gaddamanugu
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2011, 50 (11): : 1579 - 1586
  • [40] Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones
    Xu Mengmeng
    Cai Quan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (03) : 698 - 713
12345