Isocytosine
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Names | |
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IUPAC name
2-Amino-3H-pyrimidin-4-one | |
Other names
2-Aminouracil | |
Identifiers | |
108-53-2 ![]() | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:55502 ![]() |
ChEMBL | ChEMBL56260 ![]() |
ChemSpider | 60309 ![]() |
ECHA InfoCard | 100.003.266 |
PubChem | 66950 |
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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]
![](../I/m/IG-iC_DNA_base_pair.svg.png)
Isoguanine-Isocytosine-base-pair
It can be synthesized from guanidine and malic acid.[2]
![](../I/m/Synthesis_Isocytosine.svg.png)
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]
![](../I/m/Tautomerisation_of_isocytosine.svg.png)
Tautomerism of isocytosine
References
- ↑ "Isocytosine". Molecule of the Week. American Chemical Society. Retrieved November 1, 2012.
- ↑ William T. Caldwell , Harry B. Kime (1940). "A New Synthesis of Isocytosine". J. Am. Chem. Soc. 62 (9): 2365–2365. doi:10.1021/ja01866a028.
- ↑ "Isocytosine". Sigma-Aldrich. Retrieved November 1, 2012.
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