Synthesis of Threefold Glycosylated Proteins using Click Chemistry and Genetically Encoded Unnatural Amino Acids

被引:49
|
作者
Kaya, Emine [1 ]
Gutsmiedl, Katrin [1 ]
Vrabel, Milan [1 ]
Mueller, Markus [1 ]
Thumbs, Peter [1 ]
Carell, Thomas [1 ]
机构
[1] Ludwig Maximilians Univ Munchen, Dept Chem & Biochem, Ctr Integrated Prot Sci CiPSM, D-81377 Munich, Germany
关键词
amber suppression; amino acids; click chemistry; protein glycosylation; pyrrolysine; TRANSFER-RNA SYNTHETASE; SITE-SPECIFIC INCORPORATION; NATIVE CHEMICAL LIGATION; GLYCOPROTEIN-SYNTHESIS; RECOMBINANT PROTEINS; TERMINAL ALKYNES; SOLID-PHASE; PYRROLYSINE; CODE; AZIDES;
D O I
10.1002/cbic.200900625
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Click to convert. Three encoded alkyne and alkene amino acids were incorporated into yellow fluorescent protein (YFP) and subsequently glycosylated by using the CuI catalyzed click reaction, as illustrated in the scheme. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2858 / 2861
页数:4
相关论文
共 50 条
  • [21] A computational method to predict genetically encoded rare amino acids in proteins
    Barnali N Chaudhuri
    Todd O Yeates
    [J]. Genome Biology, 6
  • [22] Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues
    Patil, Pravin C.
    Luzzio, Frederick A.
    [J]. SYNLETT, 2017, 28 (14) : 1729 - 1732
  • [23] Genetically Encoded Copper-Free Click Chemistry
    Plass, Tilman
    Milles, Sigrid
    Koehler, Christine
    Schultz, Carsten
    Lemke, Edward A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3878 - 3881
  • [24] Genetically encoding bioreactive unnatural amino acids
    Wang, Lei
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [25] Synthesis of unnatural amino acids with new function and their incorporation into proteins
    Uprety, Rajendra
    Chou, Chungjung
    Deiters, Alexander
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [26] A NEW APPROACH TO THE SYNTHESIS OF DIPEPTIDES WITH UNNATURAL AMINO-ACIDS USING ORGANOZINC CHEMISTRY
    DUNN, MJ
    GOMEZ, S
    JACKSON, RFW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13): : 1639 - 1640
  • [27] Unnatural amino acids in enzymes and proteins
    Pojitkov, AE
    Efremenko, EN
    Varfolomeev, SD
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 10 (1-3) : 47 - 55
  • [28] Optical Control of a Neuronal Protein Using a Genetically Encoded Unnatural Amino Acid in Neurons
    Kang, Ji-Yong
    Kawaguchi, Daichi
    Wang, Lei
    [J]. JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2016, (109):
  • [29] Genetically encoded FRET sensors using a fluorescent unnatural amino acid as a FRET donor
    Ko, Wooseok
    Kim, Sanggil
    Lee, Seonghyun
    Jo, Kyubong
    Lee, Hyun Soo
    [J]. RSC ADVANCES, 2016, 6 (82): : 78661 - 78668
  • [30] Combined Use of Unnatural Amino Acids Enables Dual-Color Super-Resolution Imaging of Proteins via Click Chemistry
    Saal, Kim-A.
    Richter, Frank
    Rehling, Peter
    Rizzoli, Silvio O.
    [J]. ACS NANO, 2018, 12 (12) : 12247 - 12254