5-Hydroxymethylcytosine

5-Hydroxymethylcytosine
Skeletal formula of 5-hydroxymethylcytosine
Ball-and-stick model of the 5-hydroxymethylcytosine molecule
Names
Preferred IUPAC name
4-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10) checkY
    Key: RYVNIFSIEDRLSJ-UHFFFAOYSA-N checkY
  • InChI=1/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10)
    Key: RYVNIFSIEDRLSJ-UHFFFAOYAT
  • C1=NC(=O)NC(=C1CO)N
  • O=C1/N=C\C(=C(\N)N1)CO
Properties
C5H7N3O2
Molar mass 141.13 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

5-Hydroxymethylcytosine (5hmC) is a DNA pyrimidine nitrogen base derived from cytosine. It is potentially important in epigenetics, because the hydroxymethyl group on the cytosine can possibly switch a gene on and off. It was first seen in bacteriophages in 1952.[1][2] However, in 2009 it was found to be abundant in human and mouse brains,[3] as well as in embryonic stem cells.[4] In mammals, it can be generated by oxidation of 5-methylcytosine, a reaction mediated by TET enzymes.

  1. ^ Warren RA (1980). "Modified bases in bacteriophage DNAs". Annu. Rev. Microbiol. 34: 137–158. doi:10.1146/annurev.mi.34.100180.001033. PMID 7002022.
  2. ^ Wyatt GR, Cohen SS (December 1952). "A new pyrimidine base from bacteriophage nucleic acids". Nature. 170 (4338): 1072–1073. Bibcode:1952Natur.170.1072W. doi:10.1038/1701072a0. PMID 13013321. S2CID 4277592.
  3. ^ Kriaucionis S, Heintz N (May 2009). "The nuclear DNA base 5-hydroxymethylcytosine is present in Purkinje neurons and the brain". Science. 324 (5929): 929–930. Bibcode:2009Sci...324..929K. doi:10.1126/science.1169786. PMC 3263819. PMID 19372393.
  4. ^ Tahiliani M, et al. (May 2009). "Conversion of 5-methylcytosine to 5-hydroxymethylcytosine in mammalian DNA by MLL partner TET1" (PDF). Science. 324 (5929): 930–935. Bibcode:2009Sci...324..930T. doi:10.1126/science.1170116. PMC 2715015. PMID 19372391.