ArticleAngewandte Chemie (International ed. in English)2016
Tautomers of a Fluorescent G Surrogate and Their Distinct Photophysics Provide Additional Information Channels.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Insights into tautomerism and pH effects on the photoluminescence of citric acid-derived molecular fluorophores.RSC advances · 2026Article
- Decoding the base flipping mechanism of the SET- and RING-associated (SRA) domain of the epigenetic UHRF1 protein.Nucleic acids research · 2025Article
- Fluorescence and Photophysical Properties of Anthracene and Phenanthrene in Water.Journal of fluorescence · 2025Article
- Emissive Alkylated Guanine Analogs as Probes for MonitoringACS omega · 2024Article
- Emissive Guanosine Analog Applicable for Real-Time Live Cell Imaging.ACS chemical biology · 2024Article
- Review
- Novel Insights on Human Carbonic Anhydrase Inhibitors Based on Coumalic Acid: Design, Synthesis, Molecular Modeling Investigation, and Biological Studies.International journal of molecular sciences · 2022Article
- What Makes Thienoguanosine an Outstanding Fluorescent DNA Probe?Journal of the American Chemical Society · 2020Article
- Enzymatic Syntheses and Applications of Fluorescent Cyclic Dinucleotides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Deciphering the pH-dependence of ground- and excited-state equilibria of thienoguanine.Physical chemistry chemical physics : PCCP · 2020Article
- Enhanced SNP-sensing using DNA-templated reactions through confined hybridization of minimal substrates (CHOMS).Chemical science · 2020Article
- Probing of Nucleic Acid Structures, Dynamics, and Interactions With Environment-Sensitive Fluorescent Labels.Frontiers in chemistry · 2020Review
- Single-Molecule Detection of a Fluorescent Nucleobase Analogue via Multiphoton Excitation.The journal of physical chemistry letters · 2019Article
- Electronic Modifications of Fluorescent Cytidine Analogues Control Photophysics and Fluorescent Responses to Base Stacking and Pairing.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Chemical, computational and functional insights into the chemical stability of the Hedgehog pathway inhibitor GANT61.Journal of enzyme inhibition and medicinal chemistry · 2018Article
- Post-transcriptional labeling by using Suzuki-Miyaura cross-coupling generates functional RNA probes.Nucleic acids research · 2018Article
- Emissive Synthetic Cofactors: Enzymatic Interconversions ofAngewandte Chemie (International ed. in English) · 2018Article
- Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates.Chemical science · 2017Article
- Dynamics of Methylated Cytosine Flipping by UHRF1.Journal of the American Chemical Society · 2017Article
- Polymerase-Mediated Site-Specific Incorporation of a Synthetic Fluorescent Isomorphic G Surrogate into RNA.Angewandte Chemie (International ed. in English) · 2017Article
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Authors and funding
12 authors.
Funding
Abstract
Thienoguanosine ((th) G) is an isomorphic nucleoside analogue acting as a faithful fluorescent substitute of G, with respectable quantum yield in oligonucleotides. Photophysical analysis of (th) G reveals the existence of two ground-state tautomers with significantly shifted absorption and emission wavelengths, and high quantum yield in buffer. Using (TD)-DFT calculations, the tautomers were identified as the H1 and H3 keto-amino tautomers. When incorporated into the loop of (-)PBS, the (-)DNA copy of the HIV-1 primer binding site, both tautomers are observed and show differential sensitivity to protein binding. The red-shifted H1 tautomer is strongly favored in matched (-)/(+)PBS duplexes, while the relative emission of the H3 tautomer can be used to detect single nucleotide polymorphisms. These tautomers and their distinct environmental sensitivity provide unprecedented information channels for analyzing G residues in oligonucleotides and their complexes.
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