Isocytosine
Chemical compound that is an isomer of cytosine
From Wikipedia, the free encyclopedia
Isocytosine or 2-aminouracil is a pyrimidine base that is an isomer of cytosine. The nucleoside form is called isocytidine (iC).[1]
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| Names | |
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| Preferred IUPAC name
2-Amino-3H-pyrimidin-4-one | |
| Other names
2-Aminouracil | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.266 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C4H5N3O | |
| Molar mass | 111.104 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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It is used in combination with isoguanine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA.[2] In particular, it is used as a nucleobase of hachimoji RNA with the abbreviation rS.[3]
Synthesis
It can be synthesized from guanidine and malic acid.[4]
Isocytosine can also be obtained by condensing guanidine hydrochloride with 3-oxopropanoic acid. However, the C3 component is not storable in this case and was, therefore, replaced with malic acid. This is decarbonylated in concentrated sulfuric acid with elimination of water, thus losing carbon monoxide. The 3-oxopropanoic acid formed in situ condenses with the guanidine in the sulfuric acid solution with double elimination of water.[5]
Uses
It is also used in physical chemical studies involving metal complex binding, hydrogen bonding, and tautomerism and proton transfer effects in nucleobases.[6]
