ArticleBioconjugate chemistry2014
Two rapid catalyst-free click reactions for in vivo protein labeling of genetically encoded strained alkene/alkyne functionalities.
Article in Bioconjugate chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 70 citations in OpenAlex.
- Site-Specific Protein Bioconjugation Through Cellular Incorporation of Noncanonical Amino Acids.Angewandte Chemie (International ed. in English) · 2026Review
- Site-Specific Surface Modification via Chemoselective Click Reactions on Cyclobutene-Functionalized Monolayers.ChemistryOpen · 2026Article
- Tuning Encodable Tetrazine Chemistry for Site-Specific Protein Bioorthogonal Ligations.Angewandte Chemie (International ed. in English) · 2025Article
- Engineering Pyrrolysine Systems for Genetic Code Expansion and Reprogramming.Chemical reviews · 2024Review
- Cracking the Code: Reprogramming the Genetic Script in Prokaryotes and Eukaryotes to Harness the Power of Noncanonical Amino Acids.Chemical reviews · 2024Review
- Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes.Topics in current chemistry (Cham) · 2024Review
- An evolved pyrrolysyl-tRNA synthetase with polysubstrate specificity expands the toolbox for engineering enzymes with incorporation of noncanonical amino acids.Bioresources and bioprocessing · 2023Article
- Enhancing the performance of a mutant pyrrolysyl-tRNA synthetase to create a highly versatile eukaryotic cell-free protein synthesis tool.Scientific reports · 2023Article
- Bioorthogonal Click of Colloidal Gold Nanoparticles to Antibodies In vivo.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Profiling sirtuin activity using Copper-free click chemistry.Bioorganic chemistry · 2021Article
- Dual film-like organelles enable spatial separation of orthogonal eukaryotic translation.Cell · 2021Article
- Azide-based bioorthogonal chemistry: Reactions and its advances in cellular and biomolecular imaging.Biophysics reviews · 2021Review
- Synthesis and Evaluation of Novel Ring-Strained Noncanonical Amino Acids for Residue-Specific Bioorthogonal Reactions in Living Cells.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C-C Bond Formation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Flow Photochemical Syntheses ofIsrael journal of chemistry · 2020Article
- A Supramolecular Platform for the Introduction of Fc-Fusion Bioactive Proteins on Biomaterial Surfaces.ACS applied polymer materials · 2019Article
- Site-Specific Labeling of Proteins Using Unnatural Amino Acids.Molecules and cells · 2019Review
- Article
- Bio-orthogonal Fluorescent Labelling of Biopolymers through Inverse-Electron-Demand Diels-Alder Reactions.Chembiochem : a European journal of chemical biology · 2017Review
- Debugging Eukaryotic Genetic Code Expansion for Site-Specific Click-PAINT Super-Resolution Microscopy.Angewandte Chemie (International ed. in English) · 2016Article
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Authors and funding
9 authors at 3 institutions in 1 country.
Funding
Abstract
Detailed kinetic analyses of inverse electron-demand Diels–Alder cycloaddition and nitrilimine-alkene/alkyne 1,3-diploar cycloaddition reactions were conducted and the reactions were applied for rapid protein bioconjugation. When reacted with a tetrazine or a diaryl nitrilimine, strained alkene/alkyne entities including norbornene, trans-cyclooctene, and cyclooctyne displayed rapid kinetics. To apply these “click” reactions for site-specific protein labeling, five tyrosine derivatives that contain a norbornene, trans-cyclooctene, or cyclooctyne entity were genetically encoded into proteins in Escherichia coli using an engineered pyrrolysyl-tRNA synthetase-tRNA(CUA)(Pyl) pair. Proteins bearing these noncanonical amino acids were successively labeled with a fluorescein tetrazine dye and a diaryl nitrilimine both in vitro and in living cells.
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