ArticleChemical research in toxicology2008
Site-specific synthesis and characterization of oligonucleotides containing an N6-(2-deoxy-D-erythro-pentofuranosyl)-2,6-diamino-3,4-dihydro-4-oxo-5-N-methylformamidopyrimidine lesion, the ring-opened product from N7-methylation of deoxyguanosine.
Article in Chemical research in toxicology, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Genotoxic effects of the major alkylation damage N7-methylguanine and methyl formamidopyrimidine.The Biochemical journal · 2023Article
- Structural and functional determinants of the archaeal 8-oxoguanine-DNA glycosylase AGOG for DNA damage recognition and processing.Nucleic acids research · 2022Article
- DEB-FAPy-dG Adducts of 1,3-Butadiene: Synthesis, Structural Characterization, and Formation in 1,2,3,4-Diepoxybutane Treated DNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Sequence context effects of replication of Fapy•dG in three mutational hot spot sequences of the p53 gene in human cells.DNA repair · 2021Article
- Synthesis of Oligonucleotides Containing the NChemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Synthesis of Mitomycin C and decarbamoylmitomycin C NBioorganic chemistry · 2019Article
- Histone tails decrease N7-methyl-2'-deoxyguanosine depurination and yield DNA-protein cross-links in nucleosome core particles and cells.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Configurational and Conformational Equilibria of NChemical research in toxicology · 2018Article
- NChemical research in toxicology · 2018Article
- Chemical Biology of NChemical research in toxicology · 2017Article
- Chemical and structural characterization of interstrand cross-links formed between abasic sites and adenine residues in duplex DNA.Nucleic acids research · 2015Article
- Chemical structure and properties of interstrand cross-links formed by reaction of guanine residues with abasic sites in duplex DNA.Journal of the American Chemical Society · 2015Article
- Pyrosequencing: applicability for studying DNA damage-induced mutagenesis.Environmental and molecular mutagenesis · 2014Article
- Synthesis and characterization of oligonucleotides containing a nitrogen mustard formamidopyrimidine monoadduct of deoxyguanosine.Chemical research in toxicology · 2014Article
- Genome and cancer single nucleotide polymorphisms of the human NEIL1 DNA glycosylase: activity, structure, and the effect of editing.DNA repair · 2014Article
- Article
- Xeroderma pigmentosum complementation group C protein (XPC) serves as a general sensor of damaged DNA.DNA repair · 2013Article
- Mutagenic spectra arising from replication bypass of the 2,6-diamino-4-hydroxy-N(5)-methyl formamidopyrimidine adduct in primate cells.Chemical research in toxicology · 2013Article
- Structural and biochemical studies of a plant formamidopyrimidine-DNA glycosylase reveal why eukaryotic Fpg glycosylases do not excise 8-oxoguanine.DNA repair · 2012Article
- Replication of the 2,6-diamino-4-hydroxy-N(5)-(methyl)-formamidopyrimidine (MeFapy-dGuo) adduct by eukaryotic DNA polymerases.Chemical research in toxicology · 2012Article
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Authors and funding
6 authors.
Funding
Abstract
A phosphoramidite reagent of N6-(2-deoxy-D-erythro-pentofuranosyl)-2,6-diamino-1,4-dihydro-4-oxo-5-N-methylformamidopyrimidine (MeFapy-dGuo) lesions was synthesized in four steps from 2'-deoxyguanosine. Fapy nucleosides can rearrange to the pyranose form when the 5'-hydroxyl group is unprotected. The phosphoramidite was incorporated into oligonucleotides using solid-phase synthesis by adjusting the deprotection time for removal of the 5'-dimethoxytrityl group of the MeFapy-dGuo nucleotide, thereby minimizing its rearrangement to the ribopyranose. The furanose and pyranose forms were differentiated by a series of two-dimensional NMR experiments.
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