Bioorthogonal Reactions for Labeling Proteins

Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides

Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165

A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems

Agard, N. J., Prescher, J. A., & Bertozzi, C. R. (2004) · Journal of the American Chemical Society · doi:10.1021/ja044996f · Cited by 3,017

Cell Surface Engineering by a Modified Staudinger Reaction

Saxon, E., & Bertozzi, C. R. (2000) · Science · doi:10.1126/science.287.5460.2007 · Cited by 2,460

Copper-free click chemistry for dynamic in vivo imaging

Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., & Bertozzi, C. R. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0707090104 · Cited by 1,833

Adding New Chemistries to the Genetic Code

Liu, C. C., & Schultz, P. G. (2010) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.052308.105824 · Cited by 1,725

Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity

Blackman, M. L., Royzen, M., & Fox, J. M. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8053805 · Cited by 1,679

Chemistry in living systems

Prescher, J. A., & Bertozzi, C. R. (2005) · Nature Chemical Biology · doi:10.1038/nchembio0605-13 · Cited by 1,456

Analysis and Optimization of Copper‐Catalyzed Azide–Alkyne Cycloaddition for Bioconjugation

Hong, V., Presolski, S. I., Ma, C., & Finn, M. G. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200905087 · Cited by 1,029

In Vivo Imaging of Membrane-Associated Glycans in Developing Zebrafish

Laughlin, S. T., Baskin, J. M., Amacher, S. L., & Bertozzi, C. R. (2008) · Science · doi:10.1126/science.1155106 · Cited by 1,026

Visualizing Metabolically Labeled Glycoconjugates of Living Cells by Copper‐Free and Fast Huisgen Cycloadditions

Ning, X., Guo, J., Wolfert, M. A., & Boons, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705456 · Cited by 924

Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging

Devaraj, N. K., Weissleder, R., & Hilderbrand, S. A. (2008) · Bioconjugate Chemistry · doi:10.1021/bc8004446 · Cited by 858

Chemical remodelling of cell surfaces in living animals

Prescher, J. A., Dube, D. H., & Bertozzi, C. R. (2004) · Nature · doi:10.1038/nature02791 · Cited by 842

Engineering Chemical Reactivity on Cell Surfaces Through Oligosaccharide Biosynthesis

Mahal, L. K., Yarema, K. J., & Bertozzi, C. R. (1997) · Science · doi:10.1126/science.276.5315.1125 · Cited by 796

Profiling Enzyme Activities In Vivo Using Click Chemistry Methods

Speers, A. E., & Cravatt, B. F. (2004) · Chemistry & Biology · doi:10.1016/j.chembiol.2004.03.012 · Cited by 774

A Comparative Study of Bioorthogonal Reactions with Azides

Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A., & Bertozzi, C. R. (2006) · ACS Chemical Biology · doi:10.1021/cb6003228 · Cited by 744

Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase

Chen, I., Howarth, M., Lin, W., & Ting, A. Y. (2005) · Nature Methods · doi:10.1038/nmeth735 · Cited by 667

Encoding multiple unnatural amino acids via evolution of a quadruplet-decoding ribosome

Neumann, H., Wang, K., Davis, L., Garcia-Alai, M., & Chin, J. W. (2010) · Nature · doi:10.1038/nature08817 · Cited by 622

Bioconjugation with Strained Alkenes and Alkynes

Debets, M. F., van Berkel, S. S., Dommerholt, J., Dirks, A. (. J., Rutjes, F. P. J. T., & van Delft, F. L. (2011) · Accounts of Chemical Research · doi:10.1021/ar200059z · Cited by 564

Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry

Codelli, J. A., Baskin, J. M., Agard, N. J., & Bertozzi, C. R. (2008) · Journal of the American Chemical Society · doi:10.1021/ja803086r · Cited by 552

A chemical approach for identifying O -GlcNAc-modified proteins in cells

Vocadlo, D. J., Hang, H. C., Kim, E.-J., Hanover, J. A., & Bertozzi, C. R. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1632821100 · Cited by 538

Genetic Encoding of Bicyclononynes and trans-Cyclooctenes for Site-Specific Protein Labeling in Vitro and in Live Mammalian Cells via Rapid Fluorogenic Diels–Alder Reactions

Lang, K., Davis, L., Wallace, S., Mahesh, M., Cox, D. J., Blackman, M. L., Fox, J. M., & Chin, J. W. (2012) · Journal of the American Chemical Society · doi:10.1021/ja302832g · Cited by 523

A biocompatible condensation reaction for controlled assembly of nanostructures in living cells

Liang, G., Ren, H., & Rao, J. (2010) · Nature Chemistry · doi:10.1038/nchem.480 · Cited by 497

Genetically encoded norbornene directs site-specific cellular protein labelling via a rapid bioorthogonal reaction

Lang, K., Davis, L., Torres-Kolbus, J., Chou, C., Deiters, A., & Chin, J. W. (2012) · Nature Chemistry · doi:10.1038/nchem.1250 · Cited by 487

Bioorthogonal Turn‐On Probes for Imaging Small Molecules inside Living Cells

Devaraj, N. K., Hilderbrand, S., Upadhyay, R., Mazitschek, R., & Weissleder, R. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200906120 · Cited by 457

Increasing the Efficacy of Bioorthogonal Click Reactions for Bioconjugation: A Comparative Study

Besanceney‐Webler, C., Jiang, H., Zheng, T., Feng, L., Soriano del Amo, D., Wang, W., Klivansky, L. M., Marlow, F. L., Liu, Y., & Wu, P. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201101817 · Cited by 453

Introducing genetically encoded aldehydes into proteins

Carrico, I. S., Carlson, B. L., & Bertozzi, C. R. (2007) · Nature Chemical Biology · doi:10.1038/nchembio878 · Cited by 438

Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry

Hong, V., Steinmetz, N. F., Manchester, M., & Finn, M. G. (2010) · Bioconjugate Chemistry · doi:10.1021/bc100272z · Cited by 432

Ligand-Accelerated Cu-Catalyzed Azide−Alkyne Cycloaddition: A Mechanistic Report

Rodionov, V. O., Presolski, S. I., Díaz Díaz, D., Fokin, V. V., & Finn, M. G. (2007) · Journal of the American Chemical Society · doi:10.1021/ja072679d · Cited by 419

Cellular Consequences of Copper Complexes Used To Catalyze Bioorthogonal Click Reactions

Kennedy, D. C., McKay, C. S., Legault, M. C. B., Danielson, D. C., Blake, J. A., Pegoraro, A. F., Stolow, A., Mester, Z., & Pezacki, J. P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2083027 · Cited by 416

A Photoinducible 1,3‐Dipolar Cycloaddition Reaction for Rapid, Selective Modification of Tetrazole‐Containing Proteins

Song, W., Wang, Y., Qu, J., Madden, M. M., & Lin, Q. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705805 · Cited by 394

Biocompatible Copper(I) Catalysts for in Vivo Imaging of Glycans

Soriano del Amo, D., Wang, W., Jiang, H., Besanceney, C., Yan, A. C., Levy, M., Liu, Y., Marlow, F. L., & Wu, P. (2010) · Journal of the American Chemical Society · doi:10.1021/ja106553e · Cited by 390

Mechanistic Investigation of the Staudinger Ligation

Lin, F. L., Hoyt, H. M., van Halbeek, H., Bergman, R. G., & Bertozzi, C. R. (2005) · Journal of the American Chemical Society · doi:10.1021/ja044461m · Cited by 383

Zur Existenz niedergliedriger Cycloalkine, I

Wittig, G., & Krebs, A. (1961) · Chemische Berichte · doi:10.1002/cber.19610941213 · Cited by 369

Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine– trans- Cyclooctene Ligation

Taylor, M. T., Blackman, M. L., Dmitrenko, O., & Fox, J. M. (2011) · Journal of the American Chemical Society · doi:10.1021/ja201844c · Cited by 357

Designer proteins: applications of genetic code expansion in cell biology

Davis, L., & Chin, J. W. (2012) · Nature Reviews Molecular Cell Biology · doi:10.1038/nrm3286 · Cited by 355

Selective Functionalization of a Genetically Encoded Alkene-Containing Protein via “Photoclick Chemistry” in Bacterial Cells

Song, W., Wang, Y., Qu, J., & Lin, Q. (2008) · Journal of the American Chemical Society · doi:10.1021/ja803598e · Cited by 354

Fast, Cell‐Compatible Click Chemistry with Copper‐Chelating Azides for Biomolecular Labeling

Uttamapinant, C., Tangpeerachaikul, A., Grecian, S., Clarke, S., Singh, U., Slade, P., Gee, K. R., & Ting, A. Y. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108181 · Cited by 350

Tailored Ligand Acceleration of the Cu-Catalyzed Azide−Alkyne Cycloaddition Reaction: Practical and Mechanistic Implications

Presolski, S. I., Hong, V., Cho, S.-H., & Finn, M. G. (2010) · Journal of the American Chemical Society · doi:10.1021/ja105743g · Cited by 349

Studies on the Mechanism of Oxime and Semicarbazone Formation1

Jencks, W. P. (1959) · Journal of the American Chemical Society · doi:10.1021/ja01511a053 · Cited by 346

Amino Acids for Diels–Alder Reactions in Living Cells

Plass, T., Milles, S., Koehler, C., Szymański, J., Mueller, R., Wießler, M., Schultz, C., & Lemke, E. A. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201108231 · Cited by 341

Imaging the glycome

Laughlin, S. T., & Bertozzi, C. R. (2009) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0811481106 · Cited by 336

Multistep Engineering of Pyrrolysyl-tRNA Synthetase to Genetically Encode Nɛ-(o-Azidobenzyloxycarbonyl) lysine for Site-Specific Protein Modification

Yanagisawa, T., Ishii, R., Fukunaga, R., Kobayashi, T., Sakamoto, K., & Yokoyama, S. (2008) · Chemistry & Biology · doi:10.1016/j.chembiol.2008.10.004 · Cited by 336

Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification

Lin, Y. A., Chalker, J. M., Floyd, N., Bernardes, G. J. L., & Davis, B. G. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8026168 · Cited by 330

Residue-specific incorporation of non-canonical amino acids into proteins: recent developments and applications

Johnson, J. A., Lu, Y. Y., Van Deventer, J. A., & Tirrell, D. A. (2010) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2010.09.013 · Cited by 323

Studies on the Mechanism of Oxime and Semicarbazone Formation

JENCKS, W. P. (1968) · Organic Functional Group Analysis · doi:10.1016/b978-0-08-203484-1.50017-x · Cited by 306

Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry

Gordon, C. G., Mackey, J. L., Jewett, J. C., Sletten, E. M., Houk, K. N., & Bertozzi, C. R. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3000936 · Cited by 284

Adding l-lysine derivatives to the genetic code of mammalian cells with engineered pyrrolysyl-tRNA synthetases

Mukai, T., Kobayashi, T., Hino, N., Yanagisawa, T., Sakamoto, K., & Yokoyama, S. (2008) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2008.04.164 · Cited by 279

Genetically Encoded Photocontrol of Protein Localization in Mammalian Cells

Gautier, A., Nguyen, D. P., Lusic, H., An, W., Deiters, A., & Chin, J. W. (2010) · Journal of the American Chemical Society · doi:10.1021/ja910688s · Cited by 259

Palladium-Mediated Cell-Surface Labeling

Spicer, C. D., Triemer, T., & Davis, B. G. (2012) · Journal of the American Chemical Society · doi:10.1021/ja209352s · Cited by 259

Bioorthogonal chemistry: recent progress and future directions

Lim, R. K. V., & Lin, Q. (2010) · Chemical Communications · doi:10.1039/b925931g · Cited by 255

Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells

Liu, D. S., Tangpeerachaikul, A., Selvaraj, R., Taylor, M. T., Fox, J. M., & Ting, A. Y. (2012) · Journal of the American Chemical Society · doi:10.1021/ja209325n · Cited by 254

Expanding the Genetic Code of an Animal

Greiss, S., & Chin, J. W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2054034 · Cited by 254

Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition

Brotherton, W. S., Michaels, H. A., Simmons, J. T., Clark, R. J., Dalal, N. S., & Zhu, L. (2009) · Organic Letters · doi:10.1021/ol9021113 · Cited by 223

Chemical Technologies for Probing Glycans

Prescher, J. A., & Bertozzi, C. R. (2006) · Cell · doi:10.1016/j.cell.2006.08.017 · Cited by 215

Genetically Encoded Cyclopropene Directs Rapid, Photoclick‐Chemistry‐Mediated Protein Labeling in Mammalian Cells

Yu, Z., Pan, Y., Wang, Z., Wang, J., & Lin, Q. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201205352 · Cited by 214

Chemical Tags for Labeling Proteins Inside Living Cells

Jing, C., & Cornish, V. W. (2011) · Accounts of Chemical Research · doi:10.1021/ar200099f · Cited by 209

Expanding the genetic code of Drosophila melanogaster

Bianco, A., Townsley, F. M., Greiss, S., Lang, K., & Chin, J. W. (2012) · Nature Chemical Biology · doi:10.1038/nchembio.1043 · Cited by 198

A FRET‐Based Fluorogenic Phosphine for Live‐Cell Imaging with the Staudinger Ligation

Hangauer, M. J., & Bertozzi, C. R. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200704847 · Cited by 190

Noncanonical Amino Acids in the Interrogation of Cellular Protein Synthesis

Ngo, J. T., & Tirrell, D. A. (2011) · Accounts of Chemical Research · doi:10.1021/ar200144y · Cited by 187

Genetic Encoding of a Bicyclo[6.1.0]nonyne‐Charged Amino Acid Enables Fast Cellular Protein Imaging by Metal‐Free Ligation

Borrmann, A., Milles, S., Plass, T., Dommerholt, J., Verkade, J. M. M., Wießler, M., Schultz, C., van Hest, J. C. M., van Delft, F. L., & Lemke, E. A. (2012) · ChemBioChem · doi:10.1002/cbic.201200407 · Cited by 177

Genetically Encoded 1,2-Aminothiols Facilitate Rapid and Site-Specific Protein Labeling via a Bio-orthogonal Cyanobenzothiazole Condensation

Nguyen, D., Elliott, T., Holt, M. T., Muir, T. W., & Chin, J. W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja203111c · Cited by 175

Chemistry in Living Cells: Detection of Active Proteasomes by a Two‐Step Labeling Strategy

Ovaa, H., van Swieten, P. F., Kessler, B. M., Leeuwenburgh, M. A., Fiebiger, E., van den Nieuwendijk, A. M. C. H., Galardy, P. J., van der Marel, G. A., Ploegh, H. L., & Overkleeft, H. S. (2003) · Angewandte Chemie International Edition · doi:10.1002/anie.200351314 · Cited by 173

Olefin Cross-Metathesis on Proteins: Investigation of Allylic Chalcogen Effects and Guiding Principles in Metathesis Partner Selection

Lin, Y. A., Chalker, J. M., & Davis, B. G. (2010) · Journal of the American Chemical Society · doi:10.1021/ja104994d · Cited by 171

Chelation-Assisted, Copper(II)-Acetate-Accelerated Azide−Alkyne Cycloaddition

Kuang, G.-C., Michaels, H. A., Simmons, J. T., Clark, R. J., & Zhu, L. (2010) · The Journal of Organic Chemistry · doi:10.1021/jo101305m · Cited by 169

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. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201109252 · Cited by 163

Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes

McKay, C. S., Moran, J., & Pezacki, J. P. (2009) · Chemical Communications · doi:10.1039/b921630h · Cited by 133

Über das abgestufte Additionsvermögen von ungesättigten Ringsystemen

Alder, K., Stein, G., & Finzenhagen, H. (1931) · Justus Liebig s Annalen der Chemie · doi:10.1002/jlac.19314850113 · Cited by 125

Rapid Cross-Metathesis for Reversible Protein Modifications via Chemical Access to Se -Allyl-selenocysteine in Proteins

Lin, Y. A., Boutureira, O., Lercher, L., Bhushan, B., Paton, R. S., & Davis, B. G. (2013) · Journal of the American Chemical Society · doi:10.1021/ja403191g · Cited by 125

Self-Assembling Cytotoxins

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Selective Staudinger Modification of Proteins Containing p‐Azidophenylalanine

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Über das abgestufte Additionsvermögen von ungesättigten Ringsystemen. II

Alder, K., & Stein, G. (1933) · Justus Liebig s Annalen der Chemie · doi:10.1002/jlac.19335010102 · Cited by 94

A Metabolic Alkene Reporter for Spatiotemporally Controlled Imaging of Newly Synthesized Proteins in Mammalian Cells

Song, W., Wang, Y., Yu, Z., Vera, C. I. R., Qu, J., & Lin, Q. (2010) · ACS Chemical Biology · doi:10.1021/cb100193h · Cited by 86

Quantitative fluorescence labeling of aldehyde-tagged proteins for single-molecule imaging

Shi, X., Jung, Y., Lin, L.-J., Liu, C., Wu, C., Cann, I., & Ha, T. (2012) · Nature Methods · doi:10.1038/nmeth.1954 · Cited by 70

3 The Medicinal Chemistry of the Azido Group

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Viability study of HL60 cells in contact with commonly used microchip materials

Wolbers, F., ter Braak, P. M., Gac, S. L., Lüttge, R., Svahn, H. A., Vermes, I., & van den Berg, A. (2006) · Electrophoresis · doi:10.1002/elps.200600203 · Cited by 55

A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes

Rostovtsev, V. V., Green, L. G., Fokin, V. V., & Sharpless, K. B. (2002) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20020715)41:14<2596::aid-anie2596>3.0.co;2-4

Therapeutic Peptides: Current Applications and Future Directions

Wang, L., Wang, N., Zhang, W., Cheng, X., Yan, Z., Shao, G., Wang, X., Wang, R., & Fu, C. (2022) · Signal Transduction and Targeted Therapy · doi:10.1038/s41392-022-00904-4 · Cited by 2,131

BODIPY-based probes for the fluorescence imaging of biomolecules in living cells

Kowada, T., Maeda, H., & Kikuchi, K. (2015) · Chemical Society Reviews · doi:10.1039/c5cs00030k · Cited by 1,381

Click Chemistry in Proteomic Investigations

Parker, C. G., & Pratt, M. R. (2020) · Cell · doi:10.1016/j.cell.2020.01.025 · Cited by 380

Approaches to surface engineering of extracellular vesicles

Richter, M., Vader, P., & Fuhrmann, G. (2021) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2021.03.020 · Cited by 258

Bioorthogonal DNA Adsorption on Polydopamine Nanoparticles Mediated by Metal Coordination for Highly Robust Sensing in Serum and Living Cells

Meng, Y., Liu, P., Zhou, W., Ding, J., & Liu, J. (2018) · ACS Nano · doi:10.1021/acsnano.8b03019 · Cited by 149