ArticleBioconjugate chemistry2017
Vinyluridine as a Versatile Chemoselective Handle for the Post-transcriptional Chemical Functionalization of RNA.
Article in Bioconjugate chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 34 citations in OpenAlex.
- Enzymatic Synthesis of Modified RNA Containing 5-Methyl- or 5-Ethylpyrimidines or Substituted 7-Deazapurines and Influence of the Modifications on Stability, Translation, and CRISPR-Cas9 Cleavage.ACS chemical biology · 2025Article
- Synthesis of 2-Substituted Adenosine Triphosphate Derivatives and their use in Enzymatic Synthesis and Postsynthetic Labelling of RNA.Chembiochem : a European journal of chemical biology · 2025Article
- Detecting theBiomolecules · 2024Article
- Expedient production of site specifically nucleobase-labelled or hypermodified RNA with engineered thermophilic DNA polymerases.Nature communications · 2024Article
- Palladium-catalyzed C-H olefination of uridine, deoxyuridine, uridine monophosphate and uridine analogues.RSC advances · 2022Article
- Lights on 2,5-diaryl tetrazoles: applications and limits of a versatile photoclick reaction.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Review
- Nucleic Acid Conformation Influences Postsynthetic Suzuki-Miyaura Labeling of Oligonucleotides.Bioconjugate chemistry · 2020Article
- Bioorthogonal chemistry-based RNA labeling technologies: evolution and current state.Chemical communications (Cambridge, England) · 2020Article
- Labelling of DNA and RNA in the cellular environment by means of bioorthogonal cycloaddition chemistry.RSC chemical biology · 2020Review
- Posttranscriptional Suzuki-Miyaura Cross-Coupling Yields Labeled RNA for Conformational Analysis and Imaging.Methods in molecular biology (Clifton, N.J.) · 2020Article
- Expanding the Scope of RNA Metabolic Labeling with Vinyl Nucleosides and Inverse Electron-Demand Diels-Alder Chemistry.ACS chemical biology · 2019Article
- Article
- Post-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes.Nucleic acids research · 2018Article
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Authors and funding
2 authors at 1 institution in 1 country.
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Abstract
The development of modular and efficient methods to functionalize RNA with biophysical probes is very important in advancing the understanding of the structural and functional relevance of RNA in various cellular events. Herein, we demonstrate a two-step bioorthogonal chemical functionalization approach for the conjugation of multiple probes onto RNA transcripts using a 5-vinyl-modified uridine nucleotide analog (VUTP). VUTP, containing a structurally noninvasive and versatile chemoselective handle, was efficiently incorporated into RNA transcripts by in vitro transcription reactions. Furthermore, we show for the first time the use of a palladium-mediated oxidative Heck reaction in functionalizing RNA with fluorogenic probes by reacting vinyl-labeled RNA transcripts with appropriate boronic acid substrates. The vinyl label also permitted the post-transcriptional functionalization of RNA by a reagent-free inverse electron demand Diels-Alder (IEDDA) reaction in the presence of tetrazine substrates. Collectively, our results demonstrate that the incorporation of VUTP provides newer possibilities for the modular functionalization of RNA with variety of reporters.
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