Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.

PubWeight™: 5.34‹?› | Rank: Top 1%

🔗 View Article (PMID 12630856)

Published in J Am Chem Soc on March 19, 2003

Authors

Qian Wang1, Timothy R Chan, Robert Hilgraf, Valery V Fokin, K Barry Sharpless, M G Finn

Author Affiliations

1: Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.

Articles citing this

(truncated to the top 100)

Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl (2009) 8.15

Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions. Angew Chem Int Ed Engl (2008) 5.90

Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT). Proc Natl Acad Sci U S A (2006) 4.44

Tetrazine-based cycloadditions: application to pretargeted live cell imaging. Bioconjug Chem (2008) 3.93

Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation. Angew Chem Int Ed Engl (2009) 3.81

Second-generation difluorinated cyclooctynes for copper-free click chemistry. J Am Chem Soc (2008) 3.65

In situ visualization and dynamics of newly synthesized proteins in rat hippocampal neurons. Nat Neurosci (2010) 3.51

Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells. Proc Natl Acad Sci U S A (2007) 2.78

Interbilayer-crosslinked multilamellar vesicles as synthetic vaccines for potent humoral and cellular immune responses. Nat Mater (2011) 2.71

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. Chem Soc Rev (2010) 2.68

Applications of orthogonal "click" chemistries in the synthesis of functional soft materials. Chem Rev (2009) 2.28

Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids. Proc Natl Acad Sci U S A (2006) 2.23

Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angew Chem Int Ed Engl (2009) 2.10

Reaction discovery enabled by DNA-templated synthesis and in vitro selection. Nature (2004) 1.99

Comparative analysis of cleavable azobenzene-based affinity tags for bioorthogonal chemical proteomics. Chem Biol (2010) 1.91

Choosing an effective protein bioconjugation strategy. Nat Chem Biol (2011) 1.82

Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism. J Org Chem (2007) 1.82

Identification of protein targets of 4-hydroxynonenal using click chemistry for ex vivo biotinylation of azido and alkynyl derivatives. Chem Res Toxicol (2008) 1.82

18F labeled nanoparticles for in vivo PET-CT imaging. Bioconjug Chem (2009) 1.78

Folic acid-mediated targeting of cowpea mosaic virus particles to tumor cells. Chem Biol (2007) 1.70

Chemical probes of endocannabinoid metabolism. Pharmacol Rev (2013) 1.68

Click chemistry, a powerful tool for pharmaceutical sciences. Pharm Res (2008) 1.67

Imaging protein synthesis in cells and tissues with an alkyne analog of puromycin. Proc Natl Acad Sci U S A (2011) 1.65

Dynamic metabolic labeling of DNA in vivo with arabinosyl nucleosides. Proc Natl Acad Sci U S A (2011) 1.65

Highly fluorescent semiconducting polymer dots for biology and medicine. Angew Chem Int Ed Engl (2013) 1.63

Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells. J Am Chem Soc (2012) 1.62

Inhibitors of protein disulfide isomerase suppress apoptosis induced by misfolded proteins. Nat Chem Biol (2010) 1.62

CDK1 substitutes for mTOR kinase to activate mitotic cap-dependent protein translation. Proc Natl Acad Sci U S A (2015) 1.61

Advances in Bioconjugation. Curr Org Chem (2010) 1.60

Ultrabright and bioorthogonal labeling of cellular targets using semiconducting polymer dots and click chemistry. Angew Chem Int Ed Engl (2010) 1.59

Bioorthogonal chemistry: recent progress and future directions. Chem Commun (Camb) (2010) 1.58

Photocleavable fluorescent nucleotides for DNA sequencing on a chip constructed by site-specific coupling chemistry. Proc Natl Acad Sci U S A (2004) 1.55

Unnatural amino acid incorporation into virus-like particles. Bioconjug Chem (2008) 1.54

Bio-distribution, toxicity and pathology of cowpea mosaic virus nanoparticles in vivo. J Control Release (2007) 1.53

Fab fragment glycosylated IgG may play a central role in placental immune evasion. Hum Reprod (2014) 1.46

Viral capsid DNA aptamer conjugates as multivalent cell-targeting vehicles. J Am Chem Soc (2009) 1.43

The chemical toolbox for monitoring protein fatty acylation and prenylation. Nat Chem Biol (2010) 1.42

Click chemistry in complex mixtures: bioorthogonal bioconjugation. Chem Biol (2014) 1.40

Reversibility of covalent electrophile-protein adducts and chemical toxicity. Chem Res Toxicol (2008) 1.38

Electrophilic tuning of the chemoprotective natural product sulforaphane. Proc Natl Acad Sci U S A (2010) 1.37

Heterocyclic peptide backbone modifications in an alpha-helical coiled coil. J Am Chem Soc (2004) 1.33

The leader peptide is not required for post-translational modification by lacticin 481 synthetase. J Am Chem Soc (2007) 1.31

Two-color labeling of temporally defined protein populations in mammalian cells. Bioorg Med Chem Lett (2008) 1.30

Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research. Cancer Biother Radiopharm (2009) 1.30

Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions. J Org Chem (2007) 1.21

Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands. J Am Chem Soc (2008) 1.20

Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry. J Lipid Res (2009) 1.20

Clickable NAD analogues for labeling substrate proteins of poly(ADP-ribose) polymerases. J Am Chem Soc (2010) 1.18

"Clickable" polymer-caged nanobins as a modular drug delivery platform. J Am Chem Soc (2009) 1.18

Interaction between a 54-kilodalton mammalian cell surface protein and cowpea mosaic virus. J Virol (2006) 1.15

Polyvalent oligonucleotide iron oxide nanoparticle "click" conjugates. Nano Lett (2010) 1.09

Synthesis of a cross-linked branched polymer network in the interior of a protein cage. J Am Chem Soc (2009) 1.09

Copper-free Sonogashira cross-coupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells. J Am Chem Soc (2011) 1.08

Potato virus X as a novel platform for potential biomedical applications. Nano Lett (2010) 1.08

Bestatin-based chemical biology strategy reveals distinct roles for malaria M1- and M17-family aminopeptidases. Proc Natl Acad Sci U S A (2011) 1.07

Clickable bifunctional radiometal chelates for peptide labeling. Chem Commun (Camb) (2010) 1.06

Enzymatic aminoacylation of tRNA with unnatural amino acids. Proc Natl Acad Sci U S A (2006) 1.05

Buckyballs meet viral nanoparticles: candidates for biomedicine. J Am Chem Soc (2009) 1.04

Synthesis of fluorogenic polymers for visualizing cellular internalization. Org Lett (2008) 1.03

A two stage click-based library of protein tyrosine phosphatase inhibitors. Bioorg Med Chem (2006) 1.00

Glycopeptide-preferring polypeptide GalNAc transferase 10 (ppGalNAc T10), involved in mucin-type O-glycosylation, has a unique GalNAc-O-Ser/Thr-binding site in its catalytic domain not found in ppGalNAc T1 or T2. J Biol Chem (2009) 1.00

Crosslinking studies of protein-protein interactions in nonribosomal peptide biosynthesis. Chem Biol (2009) 1.00

Protein microarrays: novel developments and applications. Pharm Res (2010) 1.00

Mechanistic target of rapamycin (Mtor) is essential for murine embryonic heart development and growth. PLoS One (2013) 0.99

Electrochemically protected copper(I)-catalyzed azide-alkyne cycloaddition. Chembiochem (2008) 0.99

Rings, radicals, and regeneration: the early years of a bioorganic laboratory. J Org Chem (2006) 0.98

Copper-Catalyzed Azide-Alkyne Click Chemistry for Bioconjugation. Curr Protoc Chem Biol (2011) 0.98

Use of lantibiotic synthetases for the preparation of bioactive constrained peptides. Bioorg Med Chem Lett (2008) 0.98

Revisiting 30 years of biofunctionalization and surface chemistry of inorganic nanoparticles for nanomedicine. Front Chem (2014) 0.97

Concerted, rapid, quantitative, and site-specific dual labeling of proteins. J Am Chem Soc (2014) 0.97

PET imaging of bacterial infections with fluorine-18-labeled maltohexaose. Angew Chem Int Ed Engl (2014) 0.94

Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides. J Am Chem Soc (2013) 0.94

Facile preparation of fluorescent neoglycoproteins using p-nitrophenyl anthranilate as a heterobifunctional linker. Bioconjug Chem (2009) 0.94

WNT2 regulates DNA synthesis in mouse granulosa cells through beta-catenin. Biol Reprod (2010) 0.93

Purification of prenylated proteins by affinity chromatography on cyclodextrin-modified agarose. Anal Biochem (2008) 0.93

Sum of the parts: mass spectrometry-based metabolomics. Biochemistry (2013) 0.92

Advancements in the mechanistic understanding of the copper-catalyzed azide-alkyne cycloaddition. Beilstein J Org Chem (2013) 0.91

Colorimetric Cu(2+) detection using DNA-modified gold-nanoparticle aggregates as probes and click chemistry. Small (2010) 0.91

Photo-click immobilization of carbohydrates on polymeric surfaces--a quick method to functionalize surfaces for biomolecular recognition studies. Bioconjug Chem (2009) 0.91

Photo-click immobilization on quartz crystal microbalance sensors for selective carbohydrate-protein interaction analyses. Anal Chem (2010) 0.91

Chelation-assisted, copper(II)-acetate-accelerated azide-alkyne cycloaddition. J Org Chem (2010) 0.91

Expanding the substrate tolerance of biotin ligase through exploration of enzymes from diverse species. J Am Chem Soc (2008) 0.91

Lacticin 481 synthetase as a general serine/threonine kinase. ACS Chem Biol (2009) 0.91

Tags for labeling protein N-termini with subtiligase for proteomics. Bioorg Med Chem Lett (2008) 0.91

Facile and stabile linkages through tyrosine: bioconjugation strategies with the tyrosine-click reaction. Bioconjug Chem (2013) 0.90

Global amine and acid functional group modification of proteins. Anal Chem (2008) 0.90

Azido-BODIPY acid reveals quantitative Staudinger-Bertozzi ligation in two-step activity-based proteasome profiling. Chembiochem (2008) 0.90

On-chip bioorthogonal chemistry enables immobilization of in situ modified nanoparticles and small molecules for label-free monitoring of protein binding and reaction kinetics. Lab Chip (2012) 0.89

Clickable polyglycerol hyperbranched polymers and their application to gold nanoparticles and acid-labile nanocarriers. Chem Commun (Camb) (2010) 0.89

Genetically encoded unstrained olefins for live cell labeling with tetrazine dyes. Chem Commun (Camb) (2014) 0.88

Storable arylpalladium(II) reagents for alkene labeling in aqueous media. J Am Chem Soc (2011) 0.88

cat-ELCCA: a robust method to monitor the fatty acid acyltransferase activity of ghrelin O-acyltransferase (GOAT). Angew Chem Int Ed Engl (2010) 0.88

Selective gamma-ketoaldehyde scavengers protect Nav1.5 from oxidant-induced inactivation. J Mol Cell Cardiol (2009) 0.87

Clickable, hydrophilic ligand for fac-[M(I)(CO)3](+) (M = Re/(99m)Tc) applied in an S-functionalized α-MSH peptide. Bioconjug Chem (2014) 0.86

Tobacco mosaic virus as a new carrier for tumor associated carbohydrate antigens. Bioconjug Chem (2012) 0.86

Two rapid catalyst-free click reactions for in vivo protein labeling of genetically encoded strained alkene/alkyne functionalities. Bioconjug Chem (2014) 0.86

N-terminal protein modification using simple aminoacyl transferase substrates. J Am Chem Soc (2011) 0.86

Heparin antagonism by polyvalent display of cationic motifs on virus-like particles. Chembiochem (2009) 0.86

Direct measurement of cathepsin B activity in the cytosol of apoptotic cells by an activity-based probe. Chem Biol (2009) 0.86

Bio-inspired liposomal thrombomodulin conjugate through bio-orthogonal chemistry. Bioconjug Chem (2013) 0.85

Articles by these authors

A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed Engl (2002) 24.12

The growing impact of click chemistry on drug discovery. Drug Discov Today (2003) 6.79

Polytriazoles as copper(I)-stabilizing ligands in catalysis. Org Lett (2004) 5.49

Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation. Angew Chem Int Ed Engl (2009) 3.81

Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks. Angew Chem Int Ed Engl (2002) 3.06

Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J Am Chem Soc (2005) 2.75

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides. Chem Soc Rev (2010) 2.68

Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction. Angew Chem Int Ed Engl (2005) 2.62

Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J Am Chem Soc (2005) 2.35

"On water": unique reactivity of organic compounds in aqueous suspension. Angew Chem Int Ed Engl (2005) 2.21

Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(i)-catalyzed ligation of azides and alkynes. Angew Chem Int Ed Engl (2004) 2.11

Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angew Chem Int Ed Engl (2009) 2.10

Discovery and characterization of catalysts for azide-alkyne cycloaddition by fluorescence quenching. J Am Chem Soc (2004) 1.89

Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles. J Am Chem Soc (2008) 1.86

Labeling live cells by copper-catalyzed alkyne--azide click chemistry. Bioconjug Chem (2010) 1.86

Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles. J Am Chem Soc (2009) 1.85

Accelerated bioorthogonal conjugation: a practical method for the ligation of diverse functional molecules to a polyvalent virus scaffold. Bioconjug Chem (2005) 1.84

Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism. J Am Chem Soc (2008) 1.76

Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: a mechanistic report. J Am Chem Soc (2007) 1.72

A heteroaryldihydropyrimidine activates and can misdirect hepatitis B virus capsid assembly. Proc Natl Acad Sci U S A (2005) 1.72

Folic acid-mediated targeting of cowpea mosaic virus particles to tumor cells. Chem Biol (2007) 1.70

A sulfilimine bond identified in collagen IV. Science (2009) 1.69

Label-free quantification of membrane-ligand interactions using backscattering interferometry. Nat Biotechnol (2011) 1.67

Iterative in situ click chemistry creates antibody-like protein-capture agents. Angew Chem Int Ed Engl (2009) 1.64

Natural supramolecular building blocks. Wild-type cowpea mosaic virus. Chem Biol (2002) 1.64

Viral MRI contrast agents: coordination of Gd by native virions and attachment of Gd complexes by azide-alkyne cycloaddition. Chem Commun (Camb) (2007) 1.63

Inhibitors of HIV-1 protease by using in situ click chemistry. Angew Chem Int Ed Engl (2006) 1.63

In situ click chemistry: enzyme inhibitors made to their own specifications. J Am Chem Soc (2004) 1.61

Global structural changes in hepatitis B virus capsids induced by the assembly effector HAP1. J Virol (2006) 1.59

Tailored ligand acceleration of the Cu-catalyzed azide-alkyne cycloaddition reaction: practical and mechanistic implications. J Am Chem Soc (2010) 1.56

Designing facial amphiphiles for the stabilization of integral membrane proteins. Angew Chem Int Ed Engl (2007) 1.55

Crosslinking of and coupling to viral capsid proteins by tyrosine oxidation. Chem Biol (2004) 1.55

Unnatural amino acid incorporation into virus-like particles. Bioconjug Chem (2008) 1.54

Systemic trafficking of plant virus nanoparticles in mice via the oral route. Virology (2005) 1.53

Bio-distribution, toxicity and pathology of cowpea mosaic virus nanoparticles in vivo. J Control Release (2007) 1.53

A potent and highly selective inhibitor of human alpha-1,3-fucosyltransferase via click chemistry. J Am Chem Soc (2003) 1.53

Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation. Proc Natl Acad Sci U S A (2004) 1.52

Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition. J Am Chem Soc (2007) 1.50

Icosahedral virus particles as addressable nanoscale building blocks. Angew Chem Int Ed Engl (2002) 1.49

A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides. Angew Chem Int Ed Engl (2002) 1.48

In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors. J Am Chem Soc (2005) 1.47

Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes. J Am Chem Soc (2010) 1.45

Hybrid virus-polymer materials. 1. Synthesis and properties of PEG-decorated cowpea mosaic virus. Biomacromolecules (2003) 1.42

Plasma clearance of bacteriophage Qbeta particles as a function of surface charge. J Am Chem Soc (2008) 1.41

In situ click chemistry: probing the binding landscapes of biological molecules. Chem Soc Rev (2010) 1.38

Organic synthesis "on water". Chem Rev (2009) 1.37

Thiol-selective fluorogenic probes for labeling and release. J Am Chem Soc (2009) 1.36

In situ click chemistry: enzyme-generated inhibitors of carbonic anhydrase II. Angew Chem Int Ed Engl (2004) 1.35

Small-molecule effectors of hepatitis B virus capsid assembly give insight into virus life cycle. J Virol (2008) 1.34

Direct human cartilage repair using three-dimensional bioprinting technology. Tissue Eng Part A (2012) 1.33

Multivalent, bifunctional dendrimers prepared by click chemistry. Chem Commun (Camb) (2005) 1.32

Functional virus-based polymer-protein nanoparticles by atom transfer radical polymerization. J Am Chem Soc (2011) 1.30

The allylic azide rearrangement: achieving selectivity. J Am Chem Soc (2005) 1.30

Natural supramolecular building blocks. Cysteine-added mutants of cowpea mosaic virus. Chem Biol (2002) 1.29

Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides. Angew Chem Int Ed Engl (2006) 1.29

Chemical modification of viruses and virus-like particles. Curr Top Microbiol Immunol (2009) 1.28

Core-clickable PEG-branch-azide bivalent-bottle-brush polymers by ROMP: grafting-through and clicking-to. J Am Chem Soc (2010) 1.26

On-virus construction of polyvalent glycan ligands for cell-surface receptors. J Am Chem Soc (2008) 1.26

Multivalent display and receptor-mediated endocytosis of transferrin on virus-like particles. Chembiochem (2010) 1.24

Click chemistry: function follows form. Chem Soc Rev (2010) 1.23

Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition. Angew Chem Int Ed Engl (2005) 1.23

Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes. J Am Chem Soc (2011) 1.22

Trapping of hepatitis B virus capsid assembly intermediates by phenylpropenamide assembly accelerators. ACS Chem Biol (2010) 1.21

Defining criteria for oligomannose immunogens for HIV using icosahedral virus capsid scaffolds. Chem Biol (2010) 1.21

Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation. J Med Chem (2005) 1.19

Efficient synthesis of 1-sulfonyl-1,2,3-triazoles. Org Lett (2010) 1.19

Microscale NMR screening of new detergents for membrane protein structural biology. J Am Chem Soc (2008) 1.18

Refinement of structural leads for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem (2012) 1.18

Porous silicon as a versatile platform for laser desorption/ionization mass spectrometry. Anal Chem (2001) 1.16

Ruthenium-catalyzed cycloaddition of aryl azides and alkynes. Org Lett (2007) 1.16

Efficient synthesis of 2-substituted-1,2,3-triazoles. Org Lett (2008) 1.15

One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides. Org Lett (2004) 1.14

Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity. Angew Chem Int Ed Engl (2007) 1.14

New structural scaffolds for centrally acting oxime reactivators of phosphylated cholinesterases. J Biol Chem (2011) 1.14