ArticleJournal of the American Chemical Society2011
Site-specific labeling of DNA and RNA using an efficiently replicated and transcribed class of unnatural base pairs.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.
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Who cites it
42 citing papers in PubMed.
- Synthesis of a Pseudocytidine Nucleoside to Form a Stable and Selective Base Pair with Iso-guanosine in RNA.Organic letters · 2025Article
- Article
- Enzymatic Preparation of DNA with an Expanded Genetic Alphabet Using Terminal Deoxynucleotidyl Transferase and Its Applications.Methods in molecular biology (Clifton, N.J.) · 2024Article
- Phosphorothioate-Based Site-Specific Labeling of Large RNAs for Structural and Dynamic Studies.ACS chemical biology · 2022Article
- Total RNA Synthesis and its Covalent Labeling Innovation.Topics in current chemistry (Cham) · 2022Review
- Genetic Code Engineering by Natural and Unnatural Base Pair Systems for the Site-Specific Incorporation of Non-Standard Amino Acids Into Proteins.Frontiers in molecular biosciences · 2022Review
- Preparation of Site-Specifically Spin-Labeled RNA by in Vitro Transcription Using an Expanded Genetic Alphabet.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Pseudoknot length modulates the folding, conformational dynamics, and robustness of Xrn1 resistance of flaviviral xrRNAs.Nature communications · 2021Article
- Strategies for Covalent Labeling of Long RNAs.Chembiochem : a European journal of chemical biology · 2021Review
- Transcriptional processing of an unnatural base pair by eukaryotic RNA polymerase II.Nature chemical biology · 2021Article
- Reprogramming the genetic code.Nature reviews. Genetics · 2021Review
- Tag-Free Internal RNA Labeling and Photocaging Based on mRNA Methyltransferases.Angewandte Chemie (International ed. in English) · 2021Article
- Modified nucleoside triphosphates in bacterial research forRSC chemical biology · 2020Article
- Posttranscriptional site-directed spin labeling of large RNAs with an unnatural base pair system under non-denaturing conditions.Chemical science · 2020Article
- Site-specific covalent labeling of large RNAs with nanoparticles empowered by expanded genetic alphabet transcription.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- EPR Distance Measurements on Long Non-coding RNAs Empowered by Genetic Alphabet Expansion Transcription.Angewandte Chemie (International ed. in English) · 2020Article
- The Structural Basis for Processing of Unnatural Base Pairs by DNA Polymerases.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Review
- Nanopore Sequencing of an Expanded Genetic Alphabet Reveals High-Fidelity Replication of a Predominantly Hydrophobic Unnatural Base Pair.Journal of the American Chemical Society · 2020Article
- Optimization of Replication, Transcription, and Translation in a Semi-Synthetic Organism.Journal of the American Chemical Society · 2019Article
- Simple alkanoyl acylating agents for reversible RNA functionalization and control.Chemical communications (Cambridge, England) · 2019Article
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5 authors.
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Abstract
Site-specific labeling of enzymatically synthesized DNA or RNA has many potential uses in basic and applied research, ranging from facilitating biophysical studies to the in vitro evolution of functional nucleic acids and the construction of various nanomaterials and biosensors. As part of our efforts to expand the genetic alphabet, we have developed a class of unnatural base pairs, exemplified by d5SICS-dMMO2 and d5SICS-dNaM, which are efficiently replicated and transcribed, and which may be ideal for the site-specific labeling of DNA and RNA. Here, we report the synthesis and analysis of the ribo- and deoxyribo-variants, (d)5SICS and (d)MMO2, modified with free or protected propargylamine linkers that allow for the site-specific modification of DNA or RNA during or after enzymatic synthesis. We also synthesized and evaluated the α-phosphorothioate variant of d5SICSTP, which provides a route to backbone thiolation and an additional strategy for the postamplification site-specific labeling of DNA. The deoxynucleotides were characterized via steady-state kinetics and PCR, while the ribonucleosides were characterized by the transcription of both a short, model RNA as well as full length tRNA. The data reveal that while there are interesting nucleotide and polymerase-specific sensitivities to linker attachment, both (d)MMO2 and (d)5SICS may be used to produce DNA or RNA site-specifically modified with multiple, different functional groups with sufficient efficiency and fidelity for practical applications.
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