5-Formylcytosine

5-Formylcytosine
Names
	Preferred IUPAC name 4-Amino-2-oxo-1,2-dihydropyrimidine-5-carbaldehyde
Identifiers
CAS Number	4425-59-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:76794;
ChemSpider	9161502;
PubChem CID	10986305;
CompTox Dashboard (EPA)	DTXSID701336487 ;
	InChI InChI=1S/C5H5N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1-2H,(H3,6,7,8,10) Key: FHSISDGOVSHJRW-UHFFFAOYSA-N;
	SMILES C1=NC(=O)NC(=C1C=O)N;
Properties
Chemical formula	C5H5N3O2
Molar mass	139.11 g/mol
Appearance	yellow solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

5-Formylcytosine (5fC) is a pyrimidine nitrogen base derived from cytosine. In the context of nucleic acid chemistry and biology, it is regarded as an epigenetic marker. Discovered in 2011 in mammalian embryonic stem cells by Thomas Carell's research group^[1] the modified nucleoside was more recently confirmed to be relevant both as an intermediate in the active demethylation pathway and as a standalone epigenetic marker.^[2] In mammals, 5fC is formed by oxidation of 5-Hydroxymethylcytosine (5hmC) a reaction mediated by TET enzymes.^[3] Its molecular formula is C₅H₅N₃O_2.^[4]

^ Pfaffeneder, Toni; Hackner, Benjamin; Truß, Matthias; Münzel, Martin; Müller, Markus; Deiml, Christian A.; Hagemeier, Christian; Carell, Thomas (2011). "The Discovery of 5-Formylcytosine in Embryonic Stem Cell DNA". Angewandte Chemie International Edition. 50 (31): 7008–7012. doi:10.1002/anie.201103899. ISSN 1521-3773. PMID 21721093.
^ Bachman, Martin; Uribe-Lewis, Santiago; Yang, Xiaoping; Burgess, Heather E.; Iurlaro, Mario; Reik, Wolf; Murrell, Adele; Balasubramanian, Shankar (2015). "5-Formylcytosine can be a stable DNA modification in mammals". Nature Chemical Biology. 11 (8): 555–557. doi:10.1038/nchembio.1848. ISSN 1552-4469. PMC 5486442. PMID 26098680.
^ Ito, Shinsuke; Shen, Li; Dai, Qing; Wu, Susan C.; Collins, Leonard B.; Swenberg, James A.; He, Chuan; Zhang, Yi (2011-09-02). "Tet Proteins Can Convert 5-Methylcytosine to 5-Formylcytosine and 5-Carboxylcytosine". Science. 333 (6047): 1300–1303. Bibcode:2011Sci...333.1300I. doi:10.1126/science.1210597. ISSN 0036-8075. PMC 3495246. PMID 21778364.
^ PubChem. "5-Formylcytosine". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-07-26.

[1] Pfaffeneder, Toni; Hackner, Benjamin; Truß, Matthias; Münzel, Martin; Müller, Markus; Deiml, Christian A.; Hagemeier, Christian; Carell, Thomas (2011). "The Discovery of 5-Formylcytosine in Embryonic Stem Cell DNA". Angewandte Chemie International Edition. 50 (31): 7008–7012. doi:10.1002/anie.201103899. ISSN 1521-3773. PMID 21721093.

[:0-2] Bachman, Martin; Uribe-Lewis, Santiago; Yang, Xiaoping; Burgess, Heather E.; Iurlaro, Mario; Reik, Wolf; Murrell, Adele; Balasubramanian, Shankar (2015). "5-Formylcytosine can be a stable DNA modification in mammals". Nature Chemical Biology. 11 (8): 555–557. doi:10.1038/nchembio.1848. ISSN 1552-4469. PMC 5486442. PMID 26098680.

[3] Ito, Shinsuke; Shen, Li; Dai, Qing; Wu, Susan C.; Collins, Leonard B.; Swenberg, James A.; He, Chuan; Zhang, Yi (2011-09-02). "Tet Proteins Can Convert 5-Methylcytosine to 5-Formylcytosine and 5-Carboxylcytosine". Science. 333 (6047): 1300–1303. Bibcode:2011Sci...333.1300I. doi:10.1126/science.1210597. ISSN 0036-8075. PMC 3495246. PMID 21778364.

[4] PubChem. "5-Formylcytosine". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-07-26.

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