Measurement and theory of hydrogen bonding contribution to isosteric DNA base pairs

O Khakshoor, SE Wheeler, KN Houk… - Journal of the American …, 2012 - ACS Publications
We address the recent debate surrounding the ability of 2, 4-difluorotoluene (F), a low-
polarity mimic of thymine (T), to form a hydrogen-bonded complex with adenine in DNA. The …

Quantum-chemical ab initio Study on the Adenine-Difluorotoluene Complex - A Mimic for the Adenine-Thymine Base Pair

M Meyer, J Sühnel - Journal of Biomolecular Structure and …, 1997 - Taylor & Francis
Recent experiments have shown that difluorotoluene (F), a nonpolar isostere for thymine (T),
codes efficiently and specifically for adenine (A) in DNA replication. F has almost the same …

Further quantum mechanical evidence that difluorotoluene does not hydrogen bond

EC Sherer, SJ Bono, GC Shields - The Journal of Physical …, 2001 - ACS Publications
Calculations were run on the methylated DNA base pairs adenine: thymine and adenine:
difluorotoluene to further investigate the hydrogen-bonding properties of difluorotoluene (F) …

Free-Energy Perturbation Calculations of DNA Destabilization by Base Substitutions: The Effect of Neutral Guanine⊙ Thymine, Adenine⊙ Cytosine and Adenine⊙ …

J Florián, MF Goodman, A Warshel - The Journal of Physical …, 2000 - ACS Publications
The ability to determine the stability of non-Watson− Crick base pairs in DNA by computer
simulation is a necessary prerequisite for quantitative theoretical studies of DNA replication …

Why does substitution of thymine by 6-ethynylpyridone increase the thermostability of DNA double helices?

A Halder, A Datta, D Bhattacharyya… - The Journal of Physical …, 2014 - ACS Publications
Efficiency of 6-ethynylpyridone (E), a potential thymine (T) analogue, which forms high-
fidelity base pairs with adenine (A) and gives rise to stabler DNA duplexes, with stability …

Experimental measurement of aromatic stacking affinities in the context of duplex DNA

KM Guckian, BA Schweitzer, RXF Ren… - Journal of the …, 1996 - ACS Publications
Noncovalent interactions between aromatic molecules are widely believed to be important
contributing factors in the stabilization of organized structure in biological macromolecules …

Measuring the enthalpy of an individual hydrogen bond in a DNA duplex with nucleobase isotope editing and variable-temperature infrared spectroscopy

HC Peng, GL Castro, V Karthikeyan… - The Journal of …, 2023 - ACS Publications
The level of interest in probing the strength of noncovalent interactions in DNA duplexes is
high, as these weak forces dictate the range of suprastructures the double helix adopts …

Hydrogen bonding in DNA base pairs: reconciliation of theory and experiment

C Fonseca Guerra, FM Bickelhaupt… - Journal of the …, 2000 - ACS Publications
Up till now, there has been a significant disagreement between theory and experiment
regarding hydrogen bond lengths in Watson− Crick base pairs. To investigate the possible …

Orbital interactions and charge redistribution in weak hydrogen bonds: The Watson–Crick AT mimic adenine-2, 4-difluorotoluene

C Fonseca Guerra, FM Bickelhaupt - The Journal of chemical physics, 2003 - pubs.aip.org
The discovery by Kool and co-workers that 2, 4-difluorotoluene (F) mimics thymine (T) in
DNA replication has led to a controversy about the question if this mimic has the capability of …

Solution structure of a nonpolar, non-hydrogen-bonded base pair surrogate in DNA

KM Guckian, TR Krugh, ET Kool - Journal of the American …, 2000 - ACS Publications
We describe the structure in aqueous solution of a DNA duplex containing a base pair that is
structurally analogous to A− T but which lacks hydrogen bonds. Base analogues F (a …