Cytosine

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

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).

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