ArticleACS chemical biology2019
Addition of Isocyanide-Containing Amino Acids to the Genetic Code for Protein Labeling and Activation.
Article in ACS chemical biology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
21 citing papers in PubMed, 41 citations in OpenAlex.
- Site-Specific Protein Bioconjugation Through Cellular Incorporation of Noncanonical Amino Acids.Angewandte Chemie (International ed. in English) · 2026Review
- A Chemical Framework for Engineering Extracellular Vesicles' Biointerface to Advance Precision Therapeutics.Advanced materials (Deerfield Beach, Fla.) · 2026Review
- Creating unimolecular multivalent diversity in protein conjugates via the Passerini multicomponent bioconjugation with isocyanoproteins.Communications chemistry · 2026Article
- Combined Inductive and Dispersion Effects Enhance Bioorthogonal Reactivity of Tetrazines Toward Isonitriles.Angewandte Chemie (International ed. in English) · 2025Article
- Bioorthogonal Engineering of Cellular Microenvironments Using Isonitrile Ligations.Advanced functional materials · 2025Article
- Bioorthogonal Activation of Deep Red Photoredox Catalysis Inducing Pyroptosis.Journal of the American Chemical Society · 2025Article
- Biosynthesis of Halogenated Tryptophans for Protein Engineering Using Genetic Code Expansion.Chembiochem : a European journal of chemical biology · 2024Article
- Engineering Pyrrolysine Systems for Genetic Code Expansion and Reprogramming.Chemical reviews · 2024Review
- Applications of genetic code expansion technology in eukaryotes.Protein & cell · 2024Review
- 4-Isocyanoindole-2'-deoxyribonucleoside (4ICIN): An Isomorphic Indole Nucleoside Suitable for Inverse Electron Demand Diels-Alder Reactions.Tetrahedron letters · 2023Article
- Noncanonical amino acids as doubly bio-orthogonal handles for one-pot preparation of protein multiconjugates.Nature communications · 2023Article
- Expanding the eukaryotic genetic code with a biosynthesized 21st amino acid.Protein science : a publication of the Protein Society · 2022Article
- Unleashing the potential of noncanonical amino acid biosynthesis to create cells with precision tyrosine sulfation.Nature communications · 2022Article
- Enhanced incorporation of subnanometer tags into cellular proteins for fluorescence nanoscopy via optimized genetic code expansion.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Biosynthesis and Genetic Incorporation of 3,4-Dihydroxy-L-Phenylalanine into Proteins in Escherichia coli.Journal of molecular biology · 2022Article
- A Genetically Encoded Isonitrile Lysine for Orthogonal Bioorthogonal Labeling Schemes.Molecules (Basel, Switzerland) · 2021Article
- Site-Specific Incorporation of a Photoactivatable Fluorescent Amino Acid.Chembiochem : a European journal of chemical biology · 2021Article
- Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules.Frontiers in chemistry · 2021Review
- Review
- Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
Site-specific introduction of bioorthogonal handles into biomolecules provides powerful tools for studying and manipulating the structures and functions of proteins. Recent advances in bioorthogonal chemistry demonstrate that tetrazine-based bioorthogonal cycloaddition is a particularly useful methodology due to its high reactivity, biological selectivity, and turn-on property for fluorescence imaging. Despite its broad applications in protein labeling and imaging, utilization of tetrazine-based bioorthogonal cycloaddition has been limited to date by the requirement of a hydrophobic strained alkene reactive moiety. Circumventing this structural requirement, we report the site-specific incorporation of noncanonical amino acids (ncAAs) with a small isocyanide (or isonitrile) group into proteins in both bacterial and mammalian cells. We showed that under physiological conditions and in the absence of a catalyst these isocyanide-containing ncAAs could react selectively with tetrazine molecules via [4 + 1]-cycloaddition, thus providing a versatile bioorthogonal handle for site-specific protein labeling and protein decaging. Significantly, these bioorthogonal reactions between isocyanides and tetrazines also provide a unique mechanism for the activation of tetrazine-quenched fluorophores. The addition of these isocyanide-containing ncAAs to the list of 20 commonly used, naturally occurring amino acids expands our repertoire of reagents for bioorthogonal chemistry, therefore enabling new biological applications ranging from protein labeling and imaging studies to the chemical activation of proteins.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.