ArticleNucleic acids research2018
Post-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes.
Article in Nucleic acids research, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed, 51 citations in OpenAlex.
- Enzymatic synthesis of reactive RNA probes containing squaramate-linked cytidine or adenosine for bioconjugations and cross-linking with lysine-containing peptides and proteins.Communications chemistry · 2025Article
- Chemo-enzymatic production of base-modified ATP analogues for polyadenylation of RNA.Chemical science · 2024Article
- Late-stage guanine C8-H alkylation of nucleosides, nucleotides, and oligonucleotides via photo-mediated Minisci reaction.Nature communications · 2024Article
- Aqueous Activation of RNA 2'-OH for Conjugation with Amines and Thiols.Bioconjugate chemistry · 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
- Chloroacetamide-Modified Nucleotide and RNA for Bioconjugations and Cross-Linking with RNA-Binding Proteins.Angewandte Chemie (International ed. in English) · 2023Article
- Aryl diazonium intermediates enable mild DNA-compatible C-C bond formation for medicinally relevant combinatorial library synthesis.Chemical science · 2022Article
- 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
- Multiplexed CuAAC Suzuki-Miyaura Labeling for Tandem Activity-Based Chemoproteomic Profiling.Analytical chemistry · 2021Article
- 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
- Posttranscriptional Suzuki-Miyaura Cross-Coupling Yields Labeled RNA for Conformational Analysis and Imaging.Methods in molecular biology (Clifton, N.J.) · 2020Article
- Arylation Chemistry for Bioconjugation.Angewandte Chemie (International ed. in English) · 2019Review
- Article
- Water-Soluble Leaving Group Enables Hydrophobic Functionalization of RNA.Organic letters · 2018Article
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Authors and funding
3 authors at 1 institution in 2 countries.
Funding
Abstract
Pd-catalyzed C-C bond formation, an important vertebra in the spine of synthetic chemistry, is emerging as a valuable chemoselective transformation for post-synthetic functionalization of biomacromolecules. While methods are available for labeling protein and DNA, development of an analogous procedure to label RNA by cross-coupling reactions remains a major challenge. Herein, we describe a new Pd-mediated RNA oligonucleotide (ON) labeling method that involves post-transcriptional functionalization of iodouridine-labeled RNA transcripts by using Suzuki-Miyaura cross-coupling reaction. 5-Iodouridine triphosphate (IUTP) is efficiently incorporated into RNA ONs at one or more sites by T7 RNA polymerase. Further, using a catalytic system made of Pd(OAc)2 and 2-aminopyrimidine-4,6-diol (ADHP) or dimethylamino-substituted ADHP (DMADHP), we established a modular method to functionalize iodouridine-labeled RNA ONs in the presence of various boronic acid and ester substrates under very mild conditions (37°C and pH 8.5). This method is highly chemoselective, and offers direct access to RNA ONs labeled with commonly used fluorescent and affinity tags and new fluorogenic environment-sensitive nucleoside probes in a ligand-controlled stereoselective fashion. Taken together, this simple approach of generating functional RNA ON probes by Suzuki-Miyaura coupling will be a very important addition to the resources and tools available for analyzing RNA motifs.
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