Cytosine
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| Cytosine | |
|---|---|
| |
| IUPAC name | 4-amino-3H-pyrimidin-2-one |
| Identifiers | |
| CAS number | |
| PubChem | |
| MeSH | |
| 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. 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.
History
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 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.
Chemical reactions
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.
External links
- EINECS number 200-749-5
- Computational Chemistry Wiki
- 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. PMID 10200273.
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
