Isocytosine

2-amino- pyrimidin- 4-one

White prisms

Fixed

276 ° C

Attention

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Isocytosine is a heterocyclic organic compound with a Pyrimidingrundgerüst. It is an isomer of the nucleobase cytosine, wherein amino and keto swap places. It is inter alia an integral part of the nucleosides isocytidine and Pseudoisocytidin.

Representation

Isocytosine can be obtained by condensation of guanidine hydrochloride with 3- pyruvic acid ( " formylacetate " C3H4O3 ). However, the C3 component is not storable in this case and was therefore replaced by malic acid. This is decarbonylated in concentrated sulfuric acid with elimination of water, thus loses carbon monoxide. The in situ generated 3- pyruvic acid condensed with guanidine in the sulfuric acid solution under two -fold elimination of water.

Properties

Isocytosine forms white prisms having a melting point of 276 ° C. It is tautomeric and crystallized in a 1:1 ratio of a 1H and a 3H- variant.

Use

Isocytosine is used together with isoguanine for examining unusual base pairs in the DNA.