TY  - JOUR
A1  - Neitz, Hermann
A1  - Bessi, Irene
A1  - Kachler, Valentin
A1  - Michel, Manuela
A1  - Höbartner, Claudia
T1  - Tailored tolane‐perfluorotolane assembly as supramolecular base pair replacement in DNA
JF  - Angewandte Chemie International Edition
N2  - 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.
KW  - arene-fluoroarene
KW  - artificial base pair
KW  - DNA
KW  - sSupramolecular interaction
KW  - XNA
Y1  - 2022
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-312575
VL  - 62
IS  - 1
ER  -