ArticleOrganic & biomolecular chemistry2018
NMR analyses on N-hydroxymethylated nucleobases - implications for formaldehyde toxicity and nucleic acid demethylases.
Article in Organic & biomolecular chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 54 citations in OpenAlex.
- Metabolic isotopic labeling of (deoxy)ribose enables dual neutral loss scanning for profiling nucleic acid modifications.Nucleic acids research · 2026Article
- 1-Amino-but-3-enes scavenge formaldehyde and glyoxylic acid.Communications chemistry · 2026Article
- The impact of chemical reactivity on the quality and stability of RNA-LNP pharmaceuticals.Nature reviews. Chemistry · 2025Review
- Evidence human FTO catalyses hydroxylation of N6-methyladenosine without direct formation of a demethylated product contrasting with ALKBH5/2/3 and bacterial AlkB.Nucleic acids research · 2025Article
- Revealing the catalytic mechanism of the Fe(II)/2-oxoglutarate-dependent human epigenetic modifying enzyme ALKBH5.Cell reports. Physical science · 2025Article
- Role and mechanisms of m6A demethylases in digestive system tumors.American journal of cancer research · 2025Review
- Article
- Formaldehyde quantification using gas chromatography-mass spectrometry reveals high background environmental formaldehyde levels.Scientific reports · 2024Article
- Article
- Overcoming thermostability challenges in mRNA-lipid nanoparticle systems with piperidine-based ionizable lipids.Communications biology · 2024Article
- Aldehyde-mediated inhibition of asparagine biosynthesis has implications for diabetes and alcoholism.Chemical science · 2024Article
- Isolation and detection of DNA-protein crosslinks in mammalian cells.Nucleic acids research · 2024Article
- Article
- Revealing the Catalytic Strategy of FTO.Chem catalysis · 2023Article
- Unique alcohol dehydrogenases involved in algal sugar utilization by marine bacteria.Applied microbiology and biotechnology · 2023Article
- Research Advances on the Stability of mRNA Vaccines.Viruses · 2023Review
- Chemical RNA Cross-Linking: Mechanisms, Computational Analysis, and Biological Applications.JACS Au · 2023Review
- The Storage and In-Use Stability of mRNA Vaccines and Therapeutics: Not A Cold Case.Journal of pharmaceutical sciences · 2023Review
- Formaldehyde reacts with N-terminal proline residues to give bicyclic aminals.Communications chemistry · 2023Article
- Article
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 4 countries.
Funding
Abstract
Formaldehyde is produced in cells by enzyme-catalysed demethylation reactions, including those occurring on N-methylated nucleic acids. Formaldehyde reacts with nucleobases to form N-hydroxymethylated adducts that may contribute to its toxicity/carcinogenicity when added exogenously, but the chemistry of these reactions has been incompletely defined. We report NMR studies on the reactions of formaldehyde with canonical/modified nucleobases. The results reveal that hydroxymethyl hemiaminals on endocyclic nitrogens, as observed with thymidine and uridine monophosphates, are faster to form than equivalent hemiaminals on exocyclic nitrogens; however, the exocyclic adducts, as formed with adenine, guanine and cytosine, are more stable in solution. Nucleic acid demethylase (FTO)-catalysed hydroxylation of (6-methyl)adenosine results in (6-hydroxymethyl)adenosine as the major observed product; by contrast no evidence for a stable 3-hydroxymethyl adduct was accrued with FTO-catalysed oxidation of (3-methyl)thymidine. Collectively, our results imply N-hydroxymethyled adducts of nucleic acid bases, formed either by reactions with formaldehyde or via demethylase catalysis, have substantially different stabilities, with some being sufficiently stable to have functional roles in disease or the regulation of nucleic acid/nucleobase activity.
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