Cytosine

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Cytosine
Chemical name 4-Aminopyrimidin-2(1H)-one
Chemical formula C4H5N3O
Molecular mass 111.10 g/mol
Melting point 320 - 325 C (decomp)
CAS number 71-30-7
SMILES NC1=NC(NC=C1)=O
Missing image
Cytosine_chemical_structure.png
Chemical structure of 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. 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.

Cytosine was first discovered in 1894 when it was isolated from calf thymus tissues. A structure was proposed in 1903, and was synthesized (and thus confirmed) in the laboratory in the same year.

Cytosine can be found as part of DNA, RNA, or as a part of a nucleotide. As cytosine 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.

Cytosine can also be methylated into 5-methylcytosine by an enzyme called DNA methyltransferase.

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