ArticleJournal of the American Chemical Society2009
Pairing geometry of the hydrophobic thymine analogue 2,4-difluorotoluene in duplex DNA as analyzed by X-ray crystallography.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 33 citations in OpenAlex.
- Fluorobenzene Nucleobase Analogues for Triplex-Forming Peptide Nucleic Acids.Chembiochem : a European journal of chemical biology · 2022Article
- Beyond ribose and phosphate: Selected nucleic acid modifications for structure-function investigations and therapeutic applications.Beilstein journal of organic chemistry · 2021Review
- Examining the base stacking interaction in a dinucleotide context via reversible cyclobutane dimer analogue formation under UV irradiation.RSC advances · 2013Article
- Structure, stability and function of 5-chlorouracil modified A:U and G:U base pairs.Nucleic acids research · 2013Article
- The solution structure of double helical arabino nucleic acids (ANA and 2'F-ANA): effect of arabinoses in duplex-hairpin interconversion.Nucleic acids research · 2012Article
- The steric hypothesis for DNA replication and fluorine hydrogen bonding revisited in light of structural data.Accounts of chemical research · 2012Review
- Expanding the horizon of the thymine isostere biochemistry: unique cyclobutane dimers formed by photoreaction between a thymine and a toluene residue in the dinucleotide framework.Chemistry (Weinheim an der Bergstrasse, Germany) · 2012Article
- Structural basis for differential insertion kinetics of dNMPs opposite a difluorotoluene nucleotide residue.Biochemistry · 2012Article
- Measurement and theory of hydrogen bonding contribution to isosteric DNA base pairs.Journal of the American Chemical Society · 2012Article
- Hydrogen-bonding capability of a templating difluorotoluene nucleotide residue in an RB69 DNA polymerase ternary complex.Journal of the American Chemical Society · 2011Article
- Unexpected origins of the enhanced pairing affinity of 2'-fluoro-modified RNA.Nucleic acids research · 2011Article
- The many twists and turns of DNA: template, telomere, tool, and target.Current opinion in structural biology · 2010Review
- Differential stability of 2'F-ANA*RNA and ANA*RNA hybrid duplexes: roles of structure, pseudohydrogen bonding, hydration, ion uptake and flexibility.Nucleic acids research · 2010Article
- DNA damage and interstrand cross-link formation upon irradiation of aryl iodide C-nucleotide analogues.The Journal of organic chemistry · 2010Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Certain DNA polymerases (pols) were found to efficiently insert A opposite the hydrophobic T isostere 2,4-difluorotoluene (F) and vice versa, resulting in the widely held belief that some pols rely on shape rather than H-bonding for accurate replication. Using X-ray crystallography we have analyzed the geometry of F:A pairs in duplex DNA and observed a distance between fluorine and the exocyclic amino group of A that is consistent with a H-bond, thus challenging the assumption that the F analogue is unable to engage in H-bonding as well as the steric hypothesis of DNA replication. Therefore, shape and H-bonding are inherently related, and steric constraints at a pol active site, or conferred by stacking or the DNA backbone conformation, may enable H-bonding by F.
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Registered trials
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