A genetically encoded norbornene amino acid for the mild and selective modification of proteins in a copper-free click reaction
Kaya, E.; Vrabel, M.; Deiml, C.; Prill, S.; Fluxa, V.S.; Carell, T.
Angewandte Chemie 51(18): 4466-4469
2012
ISSN/ISBN: 1521-3773
PMID: 22438179
DOI: 10.1002/anie.201109252
Accession: 051140005
Built in for clicks: A specially evolved pyrrolysyl-t Rna synthetase from Methanosarcina mazei was used to incorporate a norbornene amino acid into proteins in E. coli. This unit can be site-selectively modified under mild physiological conditions using a [3+2] cycloaddition reaction with nitrile imines (see scheme).
PDF emailed within 0-6 h: $19.90
Related References
Gutsmiedl, K.; Wirges, C.T.; Ehmke, V.; Carell, T. 2009: Copper-free "click" modification of DNA via nitrile oxide-norbornene 1,3-dipolar cycloaddition Organic Letters 11(11): 2405-2408Plass, T.; Milles, S.; Koehler, C.; Schultz, C.; Lemke, E.A. 2011: Genetically encoded copper-free click chemistry Angewandte Chemie 50(17): 3878-3881
Schneider, S.; Gattner, M.J.; Vrabel, M.; Flügel, V.; López-Carrillo, V.ón.; Prill, S.; Carell, T. 2013: Structural insights into incorporation of norbornene amino acids for click modification of proteins Chembiochem: a European Journal of Chemical Biology 14(16): 2114-2118
Kaya, E.; Gutsmiedl, K.; Vrabel, M.; Müller, M.; Thumbs, P.; Carell, T. 2009: Synthesis of threefold glycosylated proteins using click chemistry and genetically encoded unnatural amino acids Chembiochem: a European Journal of Chemical Biology 10(18): 2858-2861
VanBrunt, M.P.; Shanebeck, K.; Caldwell, Z.; Johnson, J.; Thompson, P.; Martin, T.; Dong, H.; Li, G.; Xu, H.; D'Hooge, F.; Masterson, L.; Bariola, P.; Tiberghien, A.; Ezeadi, E.; Williams, D.G.; Hartley, J.A.; Howard, P.W.; Grabstein, K.H.; Bowen, M.A.; Marelli, M. 2015: Genetically Encoded Azide Containing Amino Acid in Mammalian Cells Enables Site-Specific Antibody-Drug Conjugates Using Click Cycloaddition Chemistry Bioconjugate Chemistry 26(11): 2249-2260
Loh, C.T.; Adams, L.A.; Graham, B.; Otting, G. 2018: Genetically encoded amino acids with tert-butyl and trimethylsilyl groups for site-selective studies of proteins by NMR spectroscopy Journal of Biomolecular NMR 71(4): 287-293
Lang, K.; Davis, L.; Torres-Kolbus, J.; Chou, C.; Deiters, A.; Chin, J.W. 2012: Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction Nature Chemistry 4(4): 298-304
Knight, J.C.; Richter, S.; Wuest, M.; Way, J.D.; Wuest, F. 2013: Synthesis and evaluation of an 18F-labelled norbornene derivative for copper-free click chemistry reactions Organic and Biomolecular Chemistry 11(23): 3817-3825
Meineke, B.; Heimgärtner, J.; Craig, A.J.; Landreh, M.; Moodie, L.W.K.; Elsässer, S.J. 2021: A Genetically Encoded Picolyl Azide for Improved Live Cell Copper Click Labeling Frontiers in Chemistry 9: 768535
Naganathan, S.; Ye, S.; Sakmar, T.P.; Huber, T. 2013: Site-specific epitope tagging of G protein-coupled receptors by bioorthogonal modification of a genetically encoded unnatural amino acid Biochemistry 52(6): 1028-1036
Naganathan, S.; Ye, S.; Sakmar, T.P.; Huber, T. 2013: Site-specific epitope tagging of G protein-coupled receptors by bioorthogonal modification of a genetically encoded unnatural amino acid Biochemistry 52(6): 1028-1036
Tyagi, S.; Lemke, E.A. 2013: Genetically encoded click chemistry for single-molecule FRET of proteins Methods in Cell Biology 113: 169-187
Kim, Y.; Kim, S.H.; Ferracane, D.; Katzenellenbogen, J.A.; Schroeder, C.M. 2012: Specific labeling of zinc finger proteins using noncanonical amino acids and copper-free click chemistry Bioconjugate Chemistry 23(9): 1891-1901
Quitterer, F.; List, A.; Beck, P.; Bacher, A.; Groll, M. 2012: Biosynthesis of the 22nd genetically encoded amino acid pyrrolysine: structure and reaction mechanism of PylC at 1.5Å resolution Journal of Molecular Biology 424(5): 270-282
Dai, C.; Wang, L.; Sheng, J.; Peng, H.; Draganov, A.B.; Huang, Z.; Wang, B. 2011: The first chemical synthesis of boronic acid-modified DNA through a copper-free click reaction Chemical Communications 47(12): 3598-3600
Niu, T.F.; Cai, C.; Yi, L. 2012: A One-Pot Tandem Ugi Multicomponent Reaction (Mcr)/Click Reaction as an Efficient Protecting-Group-Free Route to 1 H -1,2,3-Triazole-Modified -Amino Acid Derivatives and Peptidomimetics Helvetica Chimica Acta 95(1): 87-99
Reddington, S.C.; Tippmann, E.M.; Jones, D.D. 2012: Residue choice defines efficiency and influence of bioorthogonal protein modification via genetically encoded strain promoted Click chemistry Chemical Communications 48(67): 8419-8421
Kugele, A.; Braun, T.S.; Widder, P.; Williams, L.; Schmidt, M.J.; Summerer, D.; Drescher, M. 2019: Site-directed spin labelling of proteins by Suzuki-Miyaura coupling via a genetically encoded aryliodide amino acid Chemical Communications 55(13): 1923-1926
Dong, J.; Wang, Y.; Xiang, Q.; Lv, X.; Weng, W.; Zeng, Q. 2013: Synthesis of Chiral Amino Acid Anilides by Ligand-Free Copper-Catalyzed Selective N -Arylation of Amino Acid Amides Advanced Synthesis and Catalysis 355(4): 692-696
Guo, J.; Meng, F.; Li, X.; Wang, M.; Wu, Y.; Jing, X.; Huang, Y. 2012: PEGylated click polypeptides synthesized by copper-free microwave-assisted thermal click polymerization for selective endotoxin removal from protein solutions Macromolecular Bioscience 12(4): 533-546