ArticleAngewandte Chemie (International ed. in English)2020
Analysis of an Active Deformylation Mechanism of 5-Formyl-deoxycytidine (fdC) in Stem Cells.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 40 citations in OpenAlex.
- 5-Formylcytosine functions as a chemical regulator of nucleosome positioning.Nature communications · 2026Article
- Visible-light-induced trifluoroacetylation reaction of electron-deficient nitrogen heterocycles.Frontiers in chemistry · 2026Article
- Aldehyde or Hydrate? Investigation into the Oxidation of 5-Formylcytosine Derivatives Using a Computational and Experimental Approach.Chembiochem : a European journal of chemical biology · 2025Article
- HR-MS Analysis of the Covalent Binding of Edaravone to 5-Formylpyrimidine Bases and a DNA Oligonucleotide Containing a 5-Formylcytidine Residue.Rapid communications in mass spectrometry : RCM · 2025Article
- Bacteriophage-related epigenetic natural and non-natural pyrimidine nucleotides and their influence on transcription with T7 RNA polymerase.Communications chemistry · 2024Article
- Homologues of epigenetic pyrimidines: 5-alkyl-, 5-hydroxyalkyl and 5-acyluracil and -cytosine nucleotides: synthesis, enzymatic incorporation into DNA and effect on transcription with bacterial RNA polymerase.RSC chemical biology · 2022Article
- The pH-Dependence of the Hydration of 5-Formylcytosine: an Experimental and Theoretical Study.Chembiochem : a European journal of chemical biology · 2022Article
- Biomimetic Iron Complex Achieves TET Enzyme Reactivity*.Angewandte Chemie (International ed. in English) · 2021Article
- Direct decarboxylation of ten-eleven translocation-produced 5-carboxylcytosine in mammalian genomes forms a new mechanism for active DNA demethylation.Chemical science · 2021Article
- Deformylation of 5-Formylcytidine in Different Cell Types.Angewandte Chemie (International ed. in English) · 2021Article
- 5-Hydroxymethyl-, 5-Formyl- and 5-Carboxydeoxycytidines as Oxidative Lesions and Epigenetic Marks.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Active turnover of DNA methylation during cell fate decisions.Nature reviews. Genetics · 2021Review
- Reversal of nucleobase methylation by dioxygenases.Nature chemical biology · 2020Review
- Retracted Article: Divergent synthesis of 5-substituted pyrimidine 2'-deoxynucleosides and their incorporation into oligodeoxynucleotides for the survey of uracil DNA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
- Analysis of an Active Deformylation Mechanism of 5-Formyl-deoxycytidine (fdC) in Stem Cells.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The removal of 5-methyl-deoxycytidine (mdC) from promoter elements is associated with reactivation of the silenced corresponding genes. It takes place through an active demethylation process involving the oxidation of mdC to 5-hydroxymethyl-deoxycytidine (hmdC) and further on to 5-formyl-deoxycytidine (fdC) and 5-carboxy-deoxycytidine (cadC) with the help of α-ketoglutarate-dependent Tet oxygenases. The next step can occur through the action of a glycosylase (TDG), which cleaves fdC out of the genome for replacement by dC. A second pathway is proposed to involve C-C bond cleavage that converts fdC directly into dC. A 6-aza-5-formyl-deoxycytidine (a-fdC) probe molecule was synthesized and fed to various somatic cell lines and induced mouse embryonic stem cells, together with a 2'-fluorinated fdC analogue (F-fdC). While deformylation of F-fdC was clearly observed in vivo, it did not occur with a-fdC, thus suggesting that the C-C bond-cleaving deformylation is initiated by nucleophilic activation.
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