ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Synthesis and Evaluation of Novel Ring-Strained Noncanonical Amino Acids for Residue-Specific Bioorthogonal Reactions in Living Cells.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed.
- Efficient and Site-Specific Protein Bioconjugation Quantification in Mammalian Cells.Methods in molecular biology (Clifton, N.J.) · 2026Article
- Tuning Encodable Tetrazine Chemistry for Site-Specific Protein Bioorthogonal Ligations.Angewandte Chemie (International ed. in English) · 2025Article
- A review of conjugation technologies for antibody drug conjugates.Antibody therapeutics · 2025Review
- Strategies to Expand the Genetic Code of Mammalian Cells.Chemical reviews · 2025Review
- 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
- Late-Stage Functionalization of Living Organisms: Rethinking Selectivity in Biology.Chemical reviews · 2024Review
- Truncation-Free Genetic Code Expansion with Tetrazine Amino Acids for Quantitative Protein Ligations.Bioconjugate chemistry · 2023Article
- Genetic Code Expansion for Site-Specific Labeling of Antibodies with Radioisotopes.ACS chemical biology · 2023Article
- Quantitative Analysis and Optimization of Site-Specific Protein Bioconjugation in Mammalian Cells.Bioconjugate chemistry · 2022Article
- A dark intermediate in the fluorogenic reaction between tetrazine fluorophores andBiophysical reports · 2022Article
- Minimal genetically encoded tags for fluorescent protein labeling in living neurons.Nature communications · 2022Article
- Dual film-like organelles enable spatial separation of orthogonal eukaryotic translation.Cell · 2021Article
- 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
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Abstract
Bioorthogonal reactions are ideally suited to selectively modify proteins in complex environments, even in vivo. Kinetics and product stability of these reactions are crucial parameters to evaluate their usefulness for specific applications. Strain promoted inverse electron demand Diels-Alder cycloadditions (SPIEDAC) between tetrazines and strained alkenes or alkynes are particularly popular, as they allow ultrafast labeling inside cells. In combination with genetic code expansion (GCE)-a method that allows to incorporate noncanonical amino acids (ncAAs) site-specifically into proteins in vivo. These reactions enable residue-specific fluorophore attachment to proteins in living mammalian cells. Several SPIEDAC capable ncAAs have been presented and studied under diverse conditions, revealing different instabilities ranging from educt decomposition to product loss due to β-elimination. To identify which compounds yield the best labeling inside living mammalian cells has frequently been difficult. In this study we present a) the synthesis of four new SPIEDAC reactive ncAAs that cannot undergo β-elimination and b) a fluorescence flow cytometry based FRET-assay to measure reaction kinetics inside living cells. Our results, which at first sight can be seen conflicting with some other studies, capture GCE-specific experimental conditions, such as long-term exposure of the ring-strained ncAA to living cells, that are not taken into account in other assays.
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