Description
A nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a carboxy group.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C5H5N3O3 | 0 | 155.11150 |
Recommended notation
| Name | 5-carboxylcytosine |
|---|---|
| Abbreviation | 5caC |
| Symbol | c |
| Complement | guanine:5-carboxylcytosine |
| Symbol | 4 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 4-amino-2-oxo-1,2-dihydropyrimidine-5-carboxylic acid | Nc1nc(=O)[nH]cc1C(O)=O | InChI=1S/C5H5N3O3/c6-3-2(4(9)10)1-7-5(11)8-3/h1H,(H,9,10)(H3,6,7,8,11) | BLQMCTXZEMGOJM-UHFFFAOYSA-N |
|
Mapping techniques
| Method |
Method detail
|
Resolution
|
Qualifier
|
References |
|---|---|---|---|---|
| CAB-seq | chemical conversion | single-base |
|
MAB-seq | chemical conversion | single-base | low-input or single-cell |
|
caMAB-seq | chemical conversion | single-base |
|
nanopore | direct detection | single-base | target sequences |
|
Nature
| Origin | Function | Functional detail |
Organisms
|
References |
|---|---|---|---|---|
| natural | demethylation intermediate and possible epigenetic mark |
|
|
Citations
- Ito, S, et al. 2011. Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine. Science (New York, N.Y.). 333(6047).
- Johnson, RP, et al. 2017. Dynamics of a DNA Mismatch Site Held in Confinement Discriminate Epigenetic Modifications of Cytosine. Journal of the American Chemical Society. 139(7).
- Lu, X, et al. 2013. Chemical modification-assisted bisulfite sequencing (CAB-Seq) for 5-carboxylcytosine detection in DNA. Journal of the American Chemical Society. 135(25).
- Lu, X, et al. 2015. Base-resolution maps of 5-formylcytosine and 5-carboxylcytosine reveal genome-wide DNA demethylation dynamics. Cell Research. 25(3).
- Maiti, A, et al. 2013. Divergent mechanisms for enzymatic excision of 5-formylcytosine and 5-carboxylcytosine from DNA. Journal of the American Chemical Society. 135(42).
- Shen, L, et al. 2013. Genome-wide analysis reveals TET- and TDG-dependent 5-methylcytosine oxidation dynamics. Cell. 153(3).
- Song, CX, et al. 2013. Potential functional roles of DNA demethylation intermediates. Trends in Biochemical Sciences. 38(10).
- Wu, H, et al. 2016. Base-resolution profiling of active DNA demethylation using MAB-seq and caMAB-seq. Nature Protocols. 11(6).
- Wu, X, et al. 2017. Simultaneous mapping of active DNA demethylation and sister chromatid exchange in single cells. Genes & Development. 31(5).