ArticleJournal of the American Chemical Society2007
Fluorescent pyrimidine ribonucleotide: synthesis, enzymatic incorporation, and utilization.
Article in Journal of the American Chemical Society, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 45 papers.
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Who cites it
45 citing papers in PubMed, 161 citations in OpenAlex.
- Isothiazologuanosine (Angewandte Chemie (International ed. in English) · 2026Article
- Increased brightness of fluorescent uridine, qU, inside single- and double-stranded RNA.Scientific reports · 2026Article
- Chemo-enzymatic production of base-modified ATP analogues for polyadenylation of RNA.Chemical science · 2024Article
- Isomorphic Fluorescent Nucleosides.Accounts of chemical research · 2024Article
- Synthesis and Evaluation of Diguanosine Cap Analogs Modified at the C8-Position by Suzuki-Miyaura Cross-Coupling: Discovery of 7-Methylguanosine-Based Molecular Rotors.The Journal of organic chemistry · 2023Article
- Total RNA Synthesis and its Covalent Labeling Innovation.Topics in current chemistry (Cham) · 2022Review
- Heterocycle-modified 2'-Deoxyguanosine Nucleolipid Analogs Stabilize Guanosine Gels and Self-assemble to Form Green Fluorescent Gels.Chemistry, an Asian journal · 2022Article
- Strategies for Covalent Labeling of Long RNAs.Chembiochem : a European journal of chemical biology · 2021Review
- Stealth Fluorescence Labeling for Live Microscopy Imaging of mRNA Delivery.Journal of the American Chemical Society · 2021Article
- Modified nucleoside triphosphates in bacterial research forRSC chemical biology · 2020Article
- Bioorthogonal chemistry-based RNA labeling technologies: evolution and current state.Chemical communications (Cambridge, England) · 2020Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.The Journal of organic chemistry · 2019Article
- Post-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes.Nucleic acids research · 2018Article
- Article
- In vitro labeling strategies for in cellulo fluorescence microscopy of single ribonucleoprotein machines.Protein science : a publication of the Protein Society · 2017Article
- Vinyluridine as a Versatile Chemoselective Handle for the Post-transcriptional Chemical Functionalization of RNA.Bioconjugate chemistry · 2017Article
- Structure of the Ribosomal RNA Decoding Site Containing a Selenium-Modified Responsive Fluorescent Ribonucleoside Probe.Angewandte Chemie (International ed. in English) · 2017Article
- Polymerase-Mediated Site-Specific Incorporation of a Synthetic Fluorescent Isomorphic G Surrogate into RNA.Angewandte Chemie (International ed. in English) · 2017Article
- Enzymatic incorporation and utilization of an emissive 6-azauridine.Organic & biomolecular chemistry · 2017Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Fluorescent nucleobase analogues that respond to changes in their microenvironment are valuable for studying RNA structure, dynamics, and recognition. The most commonly used fluorescent ribonucleoside is 2-aminopurine, a highly responsive purine analogue. Responsive isosteric fluorescent pyrimidine analogues are, however, rare. Appending five-membered aromatic heterocycles at the 5-position on a pyrimidine core has recently been found to provide a family of responsive fluorescent nucleoside analogues with emission in the visible range. To explore the potential utility of this chromophore for studying RNA-ligand interactions, an efficient incorporation method is necessary. Here we describe the synthesis of the furan-containing ribonucleoside and its triphosphate, as well as their basic photophysical characteristics. We demonstrate that T7 RNA polymerase accepts this fluorescent ribonucleoside triphosphate as a substrate in in vitro transcription reactions and very efficiently incorporates it into RNA oligonucleotides, generating fluorescent constructs. Furthermore, we utilize this triphosphate for the enzymatic preparation of a fluorescent bacterial A-site, an RNA construct of potential therapeutic utility. We show that the binding of this RNA target to aminoglycoside antibiotics, its cognate ligands, can be effectively monitored by fluorescence spectroscopy. These observations are significant since isosteric emissive U derivatives are scarce and the trivial synthesis and effective enzymatic incorporation of the furan-containing U triphosphate make it accessible to the biophysical community.
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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.