Isocytosine

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Isocytosine
Isocytosine.png
Names
IUPAC name
2-Amino-3H-pyrimidin-4-one
Other names
2-Aminouracil
Identifiers
108-53-2 YesY
ChEBI CHEBI:55502 YesY
ChEMBL ChEMBL56260 YesY
ChemSpider 60309 YesY
Jmol-3D images Image
PubChem 66950
Properties
C4H5N3O
Molar mass 111.10 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

Isoguanine-Isocytosine-base-pair

It can be synthesized from guanidine and malic acid.[2]

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.[3]

Tautomerism of isocytosine

References[edit]

  1. ^ "Isocytosine". Molecule of the Week. American Chemical Society. Retrieved November 1, 2012. 
  2. ^ William T. Caldwell , Harry B. Kime (1940). "A New Synthesis of Isocytosine". J. Am. Chem. Soc. 62 (9): 2365–2365. doi:10.1021/ja01866a028. 
  3. ^ "Isocytosine". Sigma-Aldrich. Retrieved November 1, 2012.