ArticleJournal of the American Chemical Society2008
Synthesis and structure of duplex DNA containing the genotoxic nucleobase lesion N7-methylguanine.
Article in Journal of the American Chemical Society, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed, 62 citations in OpenAlex.
- Synthesis and Characterization of Chemically Stable N7-dG Estrone and Catechol Adducts.Molecules (Basel, Switzerland) · 2026Article
- Development of a Real-Time Fluorescence-Based Deamination Assay and Identification of Inhibitors of Human Cytidine Deaminase.ACS chemical biology · 2025Article
- Synthesis of Fluorinated Nucleosides/Nucleotides and Their Antiviral Properties.Molecules (Basel, Switzerland) · 2024Review
- Genotoxic effects of the major alkylation damage N7-methylguanine and methyl formamidopyrimidine.The Biochemical journal · 2023Article
- Structural Dynamics of a Common Mutagenic Oxidative DNA Lesion in Duplex DNA and during DNA Replication.Journal of the American Chemical Society · 2022Article
- Etheno adducts: from tRNA modifications to DNA adducts and back to miscoding ribonucleotides.Genes and environment : the official journal of the Japanese Environmental Mutagen Society · 2021Review
- Translesion synthesis of the major nitrogen mustard-induced DNA lesion by human DNA polymerase η.The Biochemical journal · 2020Article
- Bypass of the Major Alkylative DNA Lesion by Human DNA Polymerase η.Molecules (Basel, Switzerland) · 2019Article
- The abundant DNA adductThe Journal of biological chemistry · 2019Article
- Effect of Histone Lysine Methylation on DNA Lesion Reactivity in Nucleosome Core Particles.Chemical research in toxicology · 2019Article
- Defining the Role of Nucleotide Flipping in Enzyme Specificity UsingJournal of the American Chemical Society · 2019Article
- Structural and Kinetic Studies of the Effect of Guanine N7 Alkylation and Metal Cofactors on DNA Replication.Biochemistry · 2018Article
- Toxicity and repair of DNA adducts produced by the natural product yatakemycin.Nature chemical biology · 2017Article
- Preparation of Stable Nitrogen Mustard DNA Interstrand Cross-Link Analogs for Biochemical and Cell Biological Studies.Methods in enzymology · 2017Article
- Structural basis of damage recognition by thymine DNA glycosylase: Key roles for N-terminal residues.Nucleic acids research · 2016Article
- Article
- N7 methylation alters hydrogen-bonding patterns of guanine in duplex DNA.Journal of the American Chemical Society · 2015Article
- Structural Basis for Error-Free Bypass of the 5-N-Methylformamidopyrimidine-dG Lesion by Human DNA Polymerase η and Sulfolobus solfataricus P2 Polymerase IV.Journal of the American Chemical Society · 2015Article
- Transition-state destabilization reveals how human DNA polymerase β proceeds across the chemically unstable lesion N7-methylguanine.Nucleic acids research · 2014Article
- RNA polymerase: in search of promoters.Annals of the New York Academy of Sciences · 2013Review
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5 authors at 1 institution in 1 country.
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Abstract
The predominant product of aberrant DNA methylation is the genotoxic lesion N7-methyl-2'-deoxyguanosine (m7dG). M7dG is recognized and excised by lesion-specific DNA glycosylases, namely AlkA in E. coli and Aag in humans. Structural studies of m7dG recognition and catalysis by these enzymes have been hampered due to a lack of efficient means by which to incorporate the chemically labile m7dG moiety site-specifically into DNA on a preparative scale. Here we report a solution to this problem. We stabilized the lesion toward acid-catalyzed and glycosylase-catalyzed depurination by 2'-fluorination and toward base-catalyzed degradation using mild, nonaqueous conditions in the DNA deprotection reaction. Duplex DNA containing 2'-fluoro-m7dG (Fm7dG) cocrystallized with AlkA as a host-guest complex in which the lesion-containing segment of DNA was nearly devoid of protein contacts, thus enabling the first direct visualization of the N7-methylguanine lesion nucleobase in DNA. The structure reveals that the base-pairing mode of Fm7dG:C is nearly identical to that of G:C, and Fm7dG does not induce any apparent structural disturbance of the duplex structure. These observations suggest that AlkA and Aag must perform a structurally invasive interrogation of DNA in order to detect the presence of intrahelical m7dG lesions.
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