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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
- DOI
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10.1002/ange.202214456
- URN
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urn:nbn:de:101:1-2022120214025552102695
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:25 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Neitz, Hermann
- Bessi, Irene
- Kachler, Valentin
- Michel, Manuela
- Höbartner, Claudia
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