ArticleChemistry, an Asian journal2009
Enzymatic incorporation of emissive pyrimidine ribonucleotides.
Article in Chemistry, an Asian journal, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Development of a Real-Time Fluorescence-Based Deamination Assay and Identification of Inhibitors of Human Cytidine Deaminase.ACS chemical biology · 2025Article
- Isomorphic Fluorescent Nucleosides.Accounts of chemical research · 2024Article
- Incorporation ofInternational journal of molecular sciences · 2023Article
- Chloroacetamide-Modified Nucleotide and RNA for Bioconjugations and Cross-Linking with RNA-Binding Proteins.Angewandte Chemie (International ed. in English) · 2023Article
- Total RNA Synthesis and its Covalent Labeling Innovation.Topics in current chemistry (Cham) · 2022Review
- Therapeutic Interventions into Innate Immune Diseases by Means of Aptamers.Pharmaceutics · 2020Review
- Compatibility and Fidelity of Mirror-Image Thymidine in Transcription Events by T7 RNA Polymerase.Molecular therapy. Nucleic acids · 2020Article
- Fluorescent nucleobases as tools for studying DNA and RNA.Nature chemistry · 2017Review
- Enzymatic incorporation and utilization of an emissive 6-azauridine.Organic & biomolecular chemistry · 2017Article
- Isomorphic emissive GTP surrogate facilitates initiation and elongation of in vitro transcription reactions.Journal of the American Chemical Society · 2014Article
- Visibly emissive and responsive extended 6-aza-uridines.Organic letters · 2014Article
- Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation.Chemical communications (Cambridge, England) · 2013Article
- DNA-multichromophore systems.Chemical reviews · 2012Review
- Enzymatic incorporation of an azide-modified UTP analog into oligoribonucleotides for post-transcriptional chemical functionalization.Nature protocols · 2012Article
- Molecular evolution of functional nucleic acids with chemical modifications.Molecules (Basel, Switzerland) · 2010Review
- Fluorescent analogs of biomolecular building blocks: design, properties, and applications.Chemical reviews · 2010Review
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2 authors.
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Abstract
The enzymatic incorporation of a series of emissive pyrimidine analogues into RNA oligonucleotides is explored. T7 RNA polymerase is challenged with accepting three non-natural, yet related, triphosphates as substrates and incorporating them into diverse RNA transcripts. The three ribonucleoside triphosphates differ only in the modification of their uracil nucleus and include a thieno[3,2-d]pyrimidine nucleoside, a thieno[3,4-d]pyrimidine derivative, and a uridine containing a thiophene ring conjugated at its 5-position. All thiophene-containing uridine triphosphates (UTPs) get incorporated into RNA oligonucleotides at positions that are remote to the promoter, although the yields of the transcripts vary compared with the transcript obtained with only native triphosphates. Among the three derivatives, the 5-modified UTP is found to be the most "polymerase-friendly" and is well accommodated by T7 RNA polymerase. Although the fused thiophene analogues cannot be incorporated next to the promoter region, the 5-modified non-natural UTP gets incorporated near the promoter (albeit in relatively low yields) and even in multiple copies. Labeling experiments shed light on the mediocre incorporation of the fused analogues, suggesting the enzyme frequently pauses at the incorporation position. When incorporation does take place, the enzyme fails to elongate the modified oligonucleotide and yields aborted transcripts. Taken together, these results highlight the versatility and robustness, as well as the scope and limitation, of T7 RNA polymerase in accepting and incorporating reporter nucleotides into modified RNA transcripts.
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