Tailored Tolane‐Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA
Abstract: Arene‐fluoroarene interactions offer outstanding possibilities for engineering of supramolecular systems, including nucleic acids. Here, we implement the tolane‐perfluorotolane interaction as base pair replacement in DNA. Tolane (THH) and perfluorotolane (TFF) moieties were connected to acyclic backbone units, comprising glycol nucleic acid (GNA) or butyl nucleic acid (BuNA) building blocks, that were incorporated via phosphoramidite chemistry at opposite positions in a DNA duplex. Thermodynamic analyses by UV thermal melting revealed a compelling stabilization by THH/TFF heteropairs only when connected to the BuNA backbone, but not with the shorter GNA linker. Detailed NMR studies confirmed the preference of the BuNA backbone for enhanced polar π‐stacking. This work defines how orthogonal supramolecular interactions can be tailored by small constitutional changes in the DNA backbone, and it inspires future studies of arene‐fluoroarene‐programmed assembly of DNA.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Tailored Tolane‐Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA ; day:01 ; month:12 ; year:2022 ; extent:1
Angewandte Chemie ; (01.12.2022) (gesamt 1)
- Creator
- DOI
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10.1002/ange.202214456
- URN
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urn:nbn:de:101:1-2022120214025552102695
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:25 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Neitz, Hermann
- Bessi, Irene
- Kachler, Valentin
- Michel, Manuela
- Höbartner, Claudia
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Fundamental studies of functional nucleic acids: aptamers, riboswitches, ribozymes and DNAzymes
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Synthesis, enzymatic recognition and antiviral properties of modified purine nucleosides
Nucleic acid-mediated fluorescence activation and chromophore assembly
In vitro selected ribozymes for RNA methylation and labeling
Hydrophobic recognition motifs in functionalized DNA
Artificial Evolution of Nucleic Acid Catalysts and their Use for Studying RNA
Tailored Tolane‐Perfluorotolane Assembly as Supramolecular Base Pair Replacement in DNA
Tailored tolane‐perfluorotolane assembly as supramolecular base pair replacement in DNA
Supramolecular Fluorescence Resonance Energy Transfer in Nucleobase‐Modified Fluorogenic RNA Aptamers
Supramolecular Fluorescence Resonance Energy Transfer in Nucleobase‐Modified Fluorogenic RNA Aptamers
Supramolecular fluorescence resonance energy transfer in nucleobase-modified fluorogenic RNA aptamers
Fundamental studies of functional nucleic acids: aptamers, riboswitches, ribozymes and DNAzymes
A tolane-modified 5-ethynyluridine as a universal and fluorogenic photochemical DNA crosslinker
Synthesis, enzymatic recognition and antiviral properties of modified purine nucleosides
Nucleic acid-mediated fluorescence activation and chromophore assembly
In vitro selected ribozymes for RNA methylation and labeling
Hydrophobic recognition motifs in functionalized DNA