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Isocytosine

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Chemical compound that is an isomer of cytosine
Isocytosine
Names
Preferred IUPAC name 2-Amino-3H-pyrimidin-4-one
Other names 2-Aminouracil
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.266 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H5N3O/c5-4-6-2-1-3(8)7-4/h1-2H,(H3,5,6,7,8)Key: XQCZBXHVTFVIFE-UHFFFAOYSA-N
  • InChI=1/C4H5N3O/c5-4-6-2-1-3(8)7-4/h1-2H,(H3,5,6,7,8)Key: XQCZBXHVTFVIFE-UHFFFAOYAD
SMILES
  • O=C1/C=C\N=C(\N)N1
Properties
Chemical formula C4H5N3O
Molar mass 111.104 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Isocytosine or 2-aminouracil is a pyrimidine base that is an isomer of cytosine. It is used in combination with isoguanine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA. In particular, it is used as a nucleobase of hachimoji RNA.

Isoguanine-Isocytosine-base-pair

It can be synthesized from guanidine and malic acid.

Synthesis of isocytosine from malic acid

It is also used in physical chemical studies involving metal complex binding, hydrogen bonding, and tautomerism and proton transfer effects in nucleobases.

Tautomerism of isocytosine

References

  1. "Isocytosine". Molecule of the Week. American Chemical Society. Retrieved November 1, 2012.
  2. Hoshika, Shuichi; et al. (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science. 363 (6429): 884–887. doi:10.1126/science.aat0971. PMC 6413494. PMID 30792304.
  3. William T. Caldwell , Harry B. Kime (1940). "A New Synthesis of Isocytosine". J. Am. Chem. Soc. 62 (9): 2365–2365. doi:10.1021/ja01866a028.
  4. "Isocytosine". Sigma-Aldrich. Retrieved November 1, 2012.
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