Isocytosine

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Isocytosine
Isocytosine.png
Identifiers
CAS number 108-53-2 YesY
PubChem 66950
ChemSpider 60309 YesY
ChEBI CHEBI:55502 YesY
ChEMBL CHEMBL56260 YesY
Jmol-3D images Image 1
Properties
Molecular formula C4H5N3O
Molar mass 111.10 g mol−1
Except where noted otherwise, 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.