Cytosine

Cytosine is one of the 5 main nucleobases used in storing and transporting genetic information within a cell in the nucleic acids DNA and RNA.

Cytosine
IUPAC name 4-amino-3H-pyrimidin-2-one
Identifiers
  • 71-30-7
3D model (JSmol)
ECHA InfoCard 100.000.681
MeSH Cytosine
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • C1=C(NC(=O)N=C1)N
Properties
C4H5N3O
Molar mass 111.102
Melting point 320 - 325°C (decomp)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

In DNA and RNA, cytosine is paired with guanine. However, it is unstable, and can change into uracil (spontaneous deamination). This can lead to a point mutation if not repaired by the DNA repair enzymes such as uracil glycosylase, which cleaves a uracil in DNA.

Cytosine is the centre of modern genetic research into epigenetics. Methyl groups added to cytosine change the action of genes during lifetime. These changes are not inherited.[1]

References

  1. Carey, Nessa 2011. The epigenetics revolution: how modern biology is rewriting our understanding of genetics, disease and inheritance. London: Icon Books. ISBN 978-184831347-7

Other websites

  • Computational Chemistry Wiki Archived 2005-12-02 at the Wayback Machine
  • Shapiro R (1999). "Prebiotic cytosine synthesis: a critical analysis and implications for the origin of life". Proc. Natl. Acad. Sci. U.S.A. 96 (8): 4396–401. doi:10.1073/pnas.96.8.4396. PMC 16343. PMID 10200273.
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