ArticleOrganic letters2011
Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.
Article in Organic letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 46 citations in OpenAlex.
- Article
- Chemical and enzymatic modifications of 5-methylcytosine at the intersection of DNA damage, repair, and epigenetic reprogramming.PloS one · 2022Article
- Article
- Programmable site-selective labeling of oligonucleotides based on carbene catalysis.Nature communications · 2021Article
- Retracted Article: Divergent synthesis of 5-substituted pyrimidine 2'-deoxynucleosides and their incorporation into oligodeoxynucleotides for the survey of uracil DNA glycosylases.Chemical science · 2020Article
- 5-Formylcytosine Yields DNA-Protein Cross-Links in Nucleosome Core Particles.Journal of the American Chemical Society · 2017Article
- Effects of cytosine modifications on DNA flexibility and nucleosome mechanical stability.Nature communications · 2016Article
- Weakened N3 Hydrogen Bonding by 5-Formylcytosine and 5-Carboxylcytosine Reduces Their Base-Pairing Stability.ACS chemical biology · 2016Article
- Fragmentation of electrospray-produced deprotonated ions of oligodeoxyribonucleotides containing an alkylated or oxidized thymidine.Journal of the American Society for Mass Spectrometry · 2014Article
- A Chemical Probe Targets DNA 5-Formylcytosine Sites and Inhibits TDG Excision, Polymerases Bypass, and Gene Expression.Chemical science · 2014Article
- Synthesis of novel derivatives of 5-hydroxymethylcytosine and 5-formylcytosine as tools for epigenetics.Beilstein journal of organic chemistry · 2014Article
- Quantitative assessment of Tet-induced oxidation products of 5-methylcytosine in cellular and tissue DNA.Nucleic acids research · 2013Article
- Article
- 5-formylcytosine and 5-carboxylcytosine reduce the rate and substrate specificity of RNA polymerase II transcription.Nature structural & molecular biology · 2012Article
- Synthesis of DNA oligos containing 2'-deoxy-2'-fluoro-D-arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor.Tetrahedron · 2012Article
- Enzymatic analysis of Tet proteins: key enzymes in the metabolism of DNA methylation.Methods in enzymology · 2012Article
- Preparation of DNA containing 5-hydroxymethyl-2'-deoxycytidine modification through phosphoramidites with TBDMS as 5-hydroxymethyl protecting group.Current protocols in nucleic acid chemistry · 2011Article
- Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine.Science (New York, N.Y.) · 2011Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH(4) produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.
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