Cellular Incorporation of Unnatural Amino Acids and Bioorthogonal Labeling of Proteins

Progress toward the evolution of an organism with an expanded genetic code

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Noncanonical Amino Acids in the Interrogation of Cellular Protein Synthesis

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A General and Efficient Method for the Site-Specific Dual-Labeling of Proteins for Single Molecule Fluorescence Resonance Energy Transfer

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Selective Recognition of Protein Tetraserine Motifs with a Cell-Permeable, Pro-fluorescent Bis-boronic Acid

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Traceless and Site-Specific Ubiquitination of Recombinant Proteins

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In vivo incorporation of an alkyne into proteins in Escherichia coli

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Genetically encoding unnatural amino acids for cellular and neuronal studies

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

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Convenient Synthesis of Highly Functionalized Pyrazolines via Mild, Photoactivated 1,3-Dipolar Cycloaddition

Wang, Y., Rivera Vera, C. I., & Lin, Q. (2007) · Organic Letters · doi:10.1021/ol7017328 · Cited by 175

A Genetically Encoded Boronate‐Containing Amino Acid

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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

Ligand-Free Palladium-Mediated Site-Specific Protein Labeling Inside Gram-Negative Bacterial Pathogens

Li, J., Lin, S., Wang, J., Jia, S., Yang, M., Hao, Z., Zhang, X., & Chen, P. R. (2013) · Journal of the American Chemical Society · doi:10.1021/ja402424j · Cited by 172

Biosynthesis of Proteins Incorporating a Versatile Set of Phenylalanine Analogues

Kirshenbaum, K., Carrico, I. S., & Tirrell, D. A. (2002) · ChemBioChem · doi:10.1002/1439-7633(20020301)3:2/3<235::aid-cbic235>3.0.co;2-7 · Cited by 172

Genetic Encoding of Photocaged Cysteine Allows Photoactivation of TEV Protease in Live Mammalian Cells

Nguyen, D. P., Mahesh, M., Elsässer, S. J., Hancock, S. M., Uttamapinant, C., & Chin, J. W. (2014) · Journal of the American Chemical Society · doi:10.1021/ja412191m · Cited by 171

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

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

Nguyen, D. P., Elliott, T., Holt, M., Muir, T. W., & Chin, J. W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja203111c · Cited by 170

Live‐Cell Imaging of Cellular Proteins by a Strain‐Promoted Azide–Alkyne Cycloaddition

Beatty, K. E., Fisk, J. D., Smart, B. P., Lu, Y. Y., Szychowski, J., Hangauer, M. J., Baskin, J. M., Bertozzi, C. R., & Tirrell, D. A. (2010) · ChemBioChem · doi:10.1002/cbic.201000419 · Cited by 170

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

Light-Activated Kinases Enable Temporal Dissection of Signaling Networks in Living Cells

Gautier, A., Deiters, A., & Chin, J. W. (2011) · Journal of the American Chemical Society · doi:10.1021/ja1109979 · Cited by 166

Genetically Encoding Nϵ-Methyl-l-lysine in Recombinant Histones

Nguyen, D. P., Garcia Alai, M. M., Kapadnis, P. B., Neumann, H., & Chin, J. W. (2009) · Journal of the American Chemical Society · doi:10.1021/ja906603s · Cited by 164

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

Site-specific Incorporation of Keto Amino Acids into Functional G Protein-coupled Receptors Using Unnatural Amino Acid Mutagenesis

Ye, S., Köhrer, C., Huber, T., Kazmi, M., Sachdev, P., Yan, E. C. Y., Bhagat, A., RajBhandary, U. L., & Sakmar, T. P. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m707355200 · Cited by 162

Modular Strategy for the Construction of Radiometalated Antibodies for Positron Emission Tomography Based on Inverse Electron Demand Diels–Alder Click Chemistry

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Fluorogenic Azidofluoresceins for Biological Imaging

Shieh, P., Hangauer, M. J., & Bertozzi, C. R. (2012) · Journal of the American Chemical Society · doi:10.1021/ja308203h · Cited by 160

QuaNCAT: quantitating proteome dynamics in primary cells

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Thiacycloalkynes for Copper‐Free Click Chemistry

de Almeida, G., Sletten, E. M., Nakamura, H., Palaniappan, K. K., & Bertozzi, C. R. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201106325 · Cited by 158

A Phage Display System with Unnatural Amino Acids

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Exploring isonitrile-based click chemistry for ligation with biomolecules

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Amino acid substrate specificity of Escherichia coli phenylalanyl-tRNA synthetase altered by distinct mutations

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A Pyrrolysine Analogue for Site‐Specific Protein Ubiquitination

Li, X., Fekner, T., Ottesen, J. J., & Chan, M. K. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904472 · Cited by 141

Surveying polypeptide and protein domain conformation and association with FlAsH and ReAsH

Luedtke, N. W., Dexter, R. J., Fried, D. B., & Schepartz, A. (2007) · Nature Chemical Biology · doi:10.1038/nchembio.2007.49 · Cited by 140

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 139

A Designed Phenylalanyl-tRNA Synthetase Variant Allows Efficient in Vivo Incorporation of Aryl Ketone Functionality into Proteins

Datta, D., Wang, P., Carrico, I. S., Mayo, S. L., & Tirrell, D. A. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0177096 · Cited by 139

Short Tetracysteine Tags to β-Tubulin Demonstrate the Significance of Small Labels for Live Cell Imaging

Andresen, M. A., Schmitz-Salue, R., & Jakobs, S. (2004) · Molecular Biology of the Cell · doi:10.1091/mbc.e04-06-0454 · Cited by 139

Discovery of Long-Wavelength Photoactivatable Diaryltetrazoles for Bioorthogonal 1,3-Dipolar Cycloaddition Reactions

Wang, Y., Hu, W. J., Song, W., Lim, R. K. V., & Lin, Q. (2008) · Organic Letters · doi:10.1021/ol801350r · Cited by 139

The site-specific incorporation of p-iodo-L-phenylalanine into proteins for structure determination

Xie, J., Wang, L., Wu, N., Brock, A., Spraggon, G., & Schultz, P. G. (2004) · Nature Biotechnology · doi:10.1038/nbt1013 · Cited by 135

Expanding the Diversity of Unnatural Cell‐Surface Sialic Acids

Luchansky, S. J., Goon, S., & Bertozzi, C. R. (2004) · ChemBioChem · doi:10.1002/cbic.200300789 · Cited by 134

A Biosynthetic Route to Photoclick Chemistry on Proteins

Wang, J., Zhang, W., Song, W., Wang, Y., Yu, Z., Li, J., Wu, M., Wang, L., Zang, J., & Lin, Q. (2010) · Journal of the American Chemical Society · doi:10.1021/ja104350y · Cited by 132

Dynamic Fluorescent Imaging of Human Immunodeficiency Virus Type 1 Gag in Live Cells by Biarsenical Labeling

Rudner, L. A., Nydegger, S., Coren, L. V., Nagashima, K., Thali, M., & Ott, D. E. (2005) · Journal of Virology · doi:10.1128/jvi.79.7.4055-4065.2005 · Cited by 132

Second-Generation Covalent TMP-Tag for Live Cell Imaging

Chen, Z., Jing, C., Gallagher, S. S., Sheetz, M. P., & Cornish, V. W. (2012) · Journal of the American Chemical Society · doi:10.1021/ja303374p · Cited by 131

Discovery of Escherichia coli methionyl-tRNA synthetase mutants for efficient labeling of proteins with azidonorleucine in vivo

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Ketone Isosteres of 2-N-Acetamidosugars as Substrates for Metabolic Cell Surface Engineering

Hang, H. C., & Bertozzi, C. R. (2001) · Journal of the American Chemical Society · doi:10.1021/ja002962b · Cited by 131

Incorporation of Trifluoroisoleucine into Proteins in Vivo

Wang, P., Tang, Y., & Tirrell, D. A. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0298287 · Cited by 129

Fluorescence imaging of amyloid formation in living cells by a functional, tetracysteine-tagged α-synuclein

Roberti, M. J., Bertoncini, C. W., Klement, R., Jares-Erijman, E. A., & Jovin, T. M. (2007) · Nature Methods · doi:10.1038/nmeth1026 · Cited by 127

Palladium-mediated site-selective Suzuki–Miyaura protein modification at genetically encoded aryl halides

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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 126

An In Vivo Covalent TMP-Tag Based on Proximity-Induced Reactivity

Gallagher, S. S., Sable, J. E., Sheetz, M. P., & Cornish, V. W. (2009) · ACS Chemical Biology · doi:10.1021/cb900062k · Cited by 126

Probing Protein–Protein Interactions with a Genetically Encoded Photo‐crosslinking Amino Acid

Ai, H., Shen, W., Sagi, A., Chen, P. R., & Schultz, P. G. (2011) · ChemBioChem · doi:10.1002/cbic.201100194 · Cited by 125

Noncanonical Amino Acid Labeling in Vivo to Visualize and Affinity Purify Newly Synthesized Proteins in Larval Zebrafish

Hinz, F. I., Dieterich, D. C., Tirrell, D. A., & Schuman, E. M. (2011) · ACS Chemical Neuroscience · doi:10.1021/cn2000876 · Cited by 124

Self-Assembling Cytotoxins

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Preparation of the membrane-permeant biarsenicals FlAsH-EDT2 and ReAsH-EDT2 for fluorescent labeling of tetracysteine-tagged proteins

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Visualization of mRNA translation in living cells

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Photocleavable fluorescent nucleotides for DNA sequencing on a chip constructed by site-specific coupling chemistry

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A Pyrrolysine Analogue for Protein Click Chemistry

Fekner, T., Li, X., Lee, M. M., & Chan, M. K. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805420 · Cited by 118

Rapid, Photoactivatable Turn-On Fluorescent Probes Based on an Intramolecular Photoclick Reaction

Yu, Z., Ho, L. Y., & Lin, Q. (2011) · Journal of the American Chemical Society · doi:10.1021/ja204758c · Cited by 117

An Expanded Genetic Code in Mammalian Cells with a Functional Quadruplet Codon

Niu, W., Schultz, P. G., & Guo, J. (2013) · ACS Chemical Biology · doi:10.1021/cb4001662 · Cited by 116

Oxidative coupling of peptides to a virus capsid containing unnatural amino acids

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Fast copper-free click DNA ligation by the ring-strain promoted alkyne-azide cycloaddition reaction

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Patch–clamp coordinated spectroscopy shows P2X 2 receptor permeability dynamics require cytosolic domain rearrangements but not Panx-1 channels

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A Genetically Encoded Acrylamide Functionality

Lee, Y., Wu, B., Raymond, J. E., Zeng, Y., Fang, X., Wooley, K. L., & Liu, W. R. (2013) · ACS Chemical Biology · doi:10.1021/cb400267m · Cited by 109

Expanding the Genetic Code for Photoclick Chemistry in E. coli, Mammalian Cells, and A. thaliana

Li, F., Zhang, H., Sun, Y. W., Pan, Y., Zhou, J., & Wang, J. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201303477 · Cited by 107

Selective Staudinger Modification of Proteins Containing p‐Azidophenylalanine

Tsao, M., Tian, F., & Schultz, P. G. (2005) · ChemBioChem · doi:10.1002/cbic.200500314 · Cited by 105

Identification of an expanded set of translationally active methionine analogues in Escherichia coli

Kiick, K. L., Weberskirch, R., & Tirrell, D. A. (2001) · FEBS Letters · doi:10.1016/s0014-5793(01)02657-6 · Cited by 105

Genetically Engineered Fluoropolymers. Synthesis of Repetitive Polypeptides Containing p-Fluorophenylalanine residues

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Site‐Specific Functionalization of Proteins by Organopalladium Reactions

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Selective Enrichment of Azide-Containing Peptides from Complex Mixtures

Nessen, M. A., Kramer, G., Back, J. W., Baskin, J. M., Smeenk, L. E. J., de Koning, L. J., van Maarseveen, J. H., de Jong, L., Bertozzi, C. R., Hiemstra, H. C., et al. (2009) · Journal of Proteome Research · doi:10.1021/pr900257z · Cited by 103

Synthesis and In Vivo Imaging of a 18F‐Labeled PARP1 Inhibitor Using a Chemically Orthogonal Scavenger‐Assisted High‐Performance Method

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Regioselective Carbon–Carbon Bond Formation in Proteins with Palladium Catalysis; New Protein Chemistry by Organometallic Chemistry

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A Genetically Encoded Metabolically Stable Analogue of Phosphotyrosine in Escherichia coli

Xie, J., Supeková, Ľ., & Schultz, P. G. (2007) · ACS Chemical Biology · doi:10.1021/cb700083w · Cited by 101

Metabolic Glycan Imaging by Isonitrile–Tetrazine Click Chemistry

Stairs, S., Neves, A., Stöckmann, H., Wainman, Y. A., Zecchini, H. I., Brindle, K. M., & Leeper, F. J. (2013) · ChemBioChem · doi:10.1002/cbic.201300130 · Cited by 100

Attenuation of the Editing Activity of theEscherichia coliLeucyl-tRNA Synthetase Allows Incorporation of Novel Amino Acids into Proteins in Vivo

Tang, Y., & Tirrell, D. A. (2002) · Biochemistry · doi:10.1021/bi026130x · Cited by 99

Tetrazine-trans-cyclooctene ligation for the rapid construction of integrin αvβ3 targeted PET tracer based on a cyclic RGD peptide

Selvaraj, R., Liu, S., Hassink, M., Huang, C.-W., Yap, L. P., Park, R. J.-H., Fox, J. M., Li, Z., & Conti, P. S. (2011) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2011.04.116 · Cited by 96

An Engineered Aryl Azide Ligase for Site‐Specific Mapping of Protein–Protein Interactions through Photo‐Cross‐Linking

Baruah, H., Puthenveetil, S., Choi, Y., Shah, S., & Ting, A. Y. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802088 · Cited by 95

Progress Toward an Expanded Eukaryotic Genetic Code

Chin, J. W., Cropp, T. A., Chu, S., Meggers, E., & Schultz, P. G. (2003) · Chemistry & Biology · doi:10.1016/s1074-5521(03)00123-6 · Cited by 94

A method to site-specifically introduce methyllysine into proteins in E. coli

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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

Metabolic Functionalization of Recombinant Glycoproteins

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A Genetically Encoded Diazirine Photocrosslinker in Escherichia coli

Tippmann, E. M., Liu, W. R., Summerer, D., Mack, A. V., & Schultz, P. G. (2007) · ChemBioChem · doi:10.1002/cbic.200700460 · Cited by 93

Efficient introduction of alkene functionality into proteins in vivo

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In vivo incorporation of multiple unnatural amino acids through nonsense and frameshift suppression

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The Selective Incorporation of Alkenes into Proteins in Escherichia coli

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Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells

McKay, C. S., Blake, J. A., Cheng, J. Y., Foss, D. V., & Pezacki, J. P. (2011) · Chemical Communications · doi:10.1039/c1cc13808a · Cited by 92

A Fluorogenic TMP-Tag for High Signal-to-Background Intracellular Live Cell Imaging

Jing, C., & Cornish, V. W. (2013) · ACS Chemical Biology · doi:10.1021/cb300657r · Cited by 91

Application of Metal‐Free Triazole Formation in the Synthesis of Cyclic RGD–DTPA Conjugates

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Expanding the Scope of Protein Biosynthesis by Altering the Methionyl‐tRNA Synthetase Activity of a Bacterial Expression Host

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Site-Specific Incorporation of Photo-Cross-Linker and Bioorthogonal Amino Acids into Enteric Bacterial Pathogens

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De Novo Generation of Mutually Orthogonal Aminoacyl-tRNA Synthetase/tRNA Pairs

Neumann, H., Slusarczyk, A. L., & Chin, J. W. (2010) · Journal of the American Chemical Society · doi:10.1021/ja9068722 · Cited by 88

Reprogramming the genetic code: from triplet to quadruplet codes.

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

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A genetically encoded photocaged N ε -methyl- l -lysine

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Modification of Aniline Containing Proteins Using an Oxidative Coupling Strategy

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Engineering FRET Constructs Using CFP and YFP

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Expanding the Substrate Tolerance of Biotin Ligase through Exploration of Enzymes from Diverse Species

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Two-color labeling of temporally defined protein populations in mammalian cells

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A Bioorthogonal Quadricyclane Ligation

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Protein Engineering by In Vivo Incorporation of Non-Natural Amino Acids: Control of Incorporation of Methionine Analogues by Methionyl-tRNA Synthetase

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Live Cell Labeling of Native Intracellular Bacterial Receptors Using Aniline-Catalyzed Oxime Ligation

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Cellular Lipid Metabolism Is Influenced by the Coordination Environment of Copper

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