Description
A pyrimidone resulting from the formal oxidation of the alcoholic hydroxy group of 5-hydroxymethyluracil to the corresponding aldehyde. It is a major one-electron photooxidation product of thymine in oligodeoxynucleotides.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C5H4N2O3 | 0 | 140.097 |
Recommended notation
| Name | 5-formyluracil |
|---|---|
| Abbreviation | 5fU |
| Symbol | e |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde | N1C(NC=C(C1=O)C=O)=O | InChI=1S/C5H4N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1-2H,(H2,6,7,9,10) | OHAMXGZMZZWRCA-UHFFFAOYSA-N |
|
Mapping techniques
| Method |
Method detail
|
Resolution
|
Qualifier
|
References |
|---|---|---|---|---|
| Hardisty-labelling | chemical tagging | single-base | target sequences |
|
SMRT | direct detection | single-base |
|
Nature
| Origin | Function | Functional detail |
Organisms
|
References |
|---|---|---|---|---|
| natural | damage and demethylation intermediate | Homo sapiens |
|
Citations
- Belousova, EA, et al. 2013. Clustered DNA lesions containing 5-formyluracil and AP site: repair via the BER system. PloS One. 8(8).
- Belousova, EA, et al. 2015. Repair of Clustered Damage and DNA Polymerase Iota. Biochemistry. Biokhimiia. 80(8).
- Bjelland, S, et al. 2001. Cellular effects of 5-formyluracil in DNA. Mutation Research. 486(2).
- Bjelland, S, et al. 1995. Oxidation of thymine to 5-formyluracil in DNA: mechanisms of formation, structural implications, and base excision by human cell free extracts. Biochemistry. 34(45).
- Hardisty, RE, et al. 2015. Selective Chemical Labeling of Natural T Modifications in DNA. Journal of the American Chemical Society. 137(29).
- Jiang, HP, et al. 2017. Determination of formylated DNA and RNA by chemical labeling combined with mass spectrometry analysis. Analytica Chimica Acta. 981.
- Kamiya, H, et al. 2003. Mutagenicity of 5-formyluracil in mammalian cells. Nucleic Acids Symposium Series. (44).
- Kawasaki, F, et al. 2017. Genome-wide mapping of 5-hydroxymethyluracil in the eukaryote parasite Leishmania. Genome Biology. 18(1).
- Liu, P, et al. 2003. Repair of the mutagenic DNA oxidation product, 5-formyluracil. DNA Repair. 2(2).
- Masaoka, A, et al. 2000. Cellular repair mechanism of 5-formyluracil. Nucleic Acids Symposium Series. (42).
- Matsubara, M, et al. 2003. Identification and characterization of mammalian 5-formyluracil-DNA glycosylase. Nucleic Acids Research. Supplement (2001). (3).
- Pais, JE, et al. 2015. Biochemical characterization of a Naegleria TET-like oxygenase and its application in single molecule sequencing of 5-methylcytosine. Proceedings of the National Academy of Sciences of the United States of America. 112(14).
- Portalone, G, et al. 2007. An unusual syn conformation of 5-formyluracil stabilized by supramolecular interactions. Acta Crystallographica. Section C, Crystal Structure Communications. 63(Pt 11).
- Privat, EJ, et al. 1996. A proposed mechanism for the mutagenicity of 5-formyluracil. Mutation Research. 354(2).
- Rogstad, DK, et al. 2004. 5-Formyluracil-induced perturbations of DNA function. Biochemistry. 43(19).
- Samanta, B, et al. 2015. Fluorogenic Labeling of 5-Formylpyrimidine Nucleotides in DNA and RNA. Angewandte Chemie (International Ed. in English). 55(5).