Cytosine

Not to be confused with cysteine, cystine, cytisine, cytidine, or Cytosamine.
Cytosine
Names
IUPAC name
4-aminopyrimidin-2(1H)-one
Other names
4-amino-1H-pyrimidine-2-one
Identifiers
71-30-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16040 YesY
ChEMBL ChEMBL15913 YesY
ChemSpider 577 YesY
ECHA InfoCard 100.000.681
KEGG C00380 YesY
MeSH Cytosine
PubChem 597
UNII 8J337D1HZY YesY
Properties
C4H5N3O
Molar mass 111.10 g/mol
Density 1.55 g/cm3 (calculated)
Melting point 320 to 325 °C (608 to 617 °F; 593 to 598 K) (decomposes)
Acidity (pKa) 4.45 (secondary), 12.2 (primary)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Cytosine (/ˈsaɪtəˌsiːn, -ˌziːn, -ˌsɪn/;[2][3] C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in 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 discovered and named by Albrecht Kossel and Albert Neumann in 1894 when it was hydrolyzed from calf thymus tissues.[4][5] 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 1, 1998 when researchers at Oxford implemented David Deutsch's algorithm on a two qubit nuclear magnetic resonance quantum computer (NMRQC) based on cytosine.[6]

In March 2015, NASA scientists reported that, for the first time, complex DNA and RNA organic compounds of life, including uracil, cytosine and thymine, have been formed in the laboratory under outer space conditions, using starting chemicals, such as pyrimidine, found in meteorites. Pyrimidine, like polycyclic aromatic hydrocarbons (PAHs), the most carbon-rich chemical found in the Universe, may have been formed in red giants or in interstellar dust and gas clouds, according to the scientists.[7]

Chemical reactions

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

Cytosine can be found as part of DNA, as part of 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.

When found third in a codon of RNA, cytosine is synonymous with uracil, as they are interchangeable as the third base. When found as the second base in a codon, the third is always interchangeable. For example, UCU, UCC, UCA and UCG are all serine, regardless of the third base.

Cytosine can also be methylated into 5-methylcytosine by an enzyme called DNA methyltransferase or be methylated and hydroxylated to make 5-hydroxymethylcytosine. Active enzymatic deamination of cytosine or 5-methylcytosine by the APOBEC family of cytosine deaminases could have both beneficial and detrimental implications on various cellular processes as well as on organismal evolution.[8] The implications of deamination on 5-hydroxymethylcytosine, on the other hand, remains less understood.

Theoretical aspects

Cytosine has not been found in meteorites, which suggests the first strands of RNA and DNA had to look elsewhere to obtain this building block. Cytosine likely formed within some meteorite parent bodies, however did not persist within these bodies due to an effective deamination reaction into uracil.[9]

References

  1. ↑ Dawson, R.M.C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
  2. ↑ "Cytosine". Dictionary.com Unabridged. Random House.
  3. ↑ "Cytosine". Merriam-Webster Dictionary.
  4. ↑ A. Kossel and Albert Neumann (1894) "Darstellung und Spaltungsprodukte der Nucleïnsäure (Adenylsäure)" (Preparation and cleavage products of nucleic acids (adenic acid)), Berichte der Deutschen Chemischen Gesellschaft zu Berlin, 27 : 2215-2222. The name "cytosine" is coined on page 2219: " … ein Produkt von basischen Eigenschaften, für welches wir den Namen "Cytosin" vorschlagen." ( … a product with basic properties, for which we suggest the name "cytosine".)
  5. ↑ Kossel, A.; Steudel, H. Z. (1903). "Weitere Untersuchungen über das Cytosin". Physiol. Chem. 38: 49. doi:10.1515/bchm2.1903.38.1-2.49.
  6. ↑ 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. Retrieved 2007-10-18.
  7. ↑ Marlaire, Ruth (3 March 2015). "NASA Ames Reproduces the Building Blocks of Life in Laboratory". NASA. Retrieved 5 March 2015.
  8. ↑ Chahwan R.; Wontakal S.N.; Roa S. (2010). "Crosstalk between genetic and epigenetic information through cytosine deamination". Trends in Genetics. 26 (10): 443–448. doi:10.1016/j.tig.2010.07.005. PMID 20800313.
  9. ↑ Tasker, Elizabeth. "Did the Seeds of Life Come from Space?". Scientific American Blog Network. Retrieved 2016-11-24.
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