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Cytosine
Identifiers
CAS number 71-30-7 Yes check.svgY
PubChem 597
MeSH Cytosine
SMILES
InChI
InChI key OPTASPLRGRRNAP-UHFFFAOYSA-N
Properties
Molecular formula C4H5N3O
Molar mass 111.10 g/mol
Melting point

320–25 °C (decomp)

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cytosine is one of the four main bases found in DNA and RNA. It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). The nucleoside of cytosine is cytidine. In Watson-Crick base pairing, it forms three hydrogen bonds with guanine.

Contents

History

Cytosine was discovered by Albrecht Kossel in 1894 when it was hydrolysed from calf thymus tissues.[1] A structure was proposed in 1903, and was synthesized (and thus confirmed) in the laboratory in the same year.

Cytosine recently found use in quantum computation. The first time any quantum mechanical properties were harnessed to process information took place on August 1st in 1998 when researchers at Oxford implemented David Deutsch's algorithm on a two qubit NMRQC (Nuclear Magnetic Resonance Quantum Computer) based on the cytosine molecule.[2]

Chemical reactions

Cytosine with numbered components. Methylation occurs on carbon nr 5.

Cytosine can be found as part of DNA, RNA, or as a part of a nucleotide. As cytidine triphosphate (CTP), it can act as a co-factor to enzymes, and can transfer a phosphate to convert adenosine diphosphate (ADP) to adenosine triphosphate (ATP).

In DNA and RNA, cytosine is paired with guanine. However, it is inherently 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 can also be methylated into 5-methylcytosine by an enzyme called DNA methyltransferase or be methylated and hydroxylated to make 5-hydroxymethylcytosine.

References

  1. ^ Kossel, A.; Steudel, H. Z. Physiol. Chem. 1903, 38, 49
  2. ^ Jones, J.A.; M. Mosca (1998-08-01). "Implementation of a quantum algorithm on a nuclear magnetic resonance quantum computer". J.Chem.Phys 109 (109): 1648–1653. doi:10.1063/1.476739. http://www.citebase.org/abstract?id=oai%3AarXiv.org%3Aquant-ph%2F9801027. Retrieved 2007-10-18. 

External links

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Simple English

Cytosine
IUPAC name 4-amino-3H-pyrimidin-2-one
Identifiers
CAS number 71-30-7
PubChem 597
MeSH Cytosine
SMILES C1=C(NC(=O)N=C1)N
Properties
Molecular formula 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

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.

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.

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