N4-Acetylcytosine

Chemical properties

Crstalline powder

The Uses of N4-Acetylcytosine

N⁴-Acetylcytosine may be used in the preparation of cytidine. It may be used in the preparation of 1-(4-azido-4-deoxy-β-D-glucopyranosyl)cytosine.

Definition

ChEBI: N(4)-acetylcytosine is a pyrimidone that is cytosine bearing an N(4)-acetyl substituent. It is a pyrimidone, a nucleobase analogue and a member of acetamides. It is functionally related to a cytosine.

General Description

Four stable conformers of N⁴-acetylcytosine, and the one of the stable form containing an intramoleuclar six-membered ring have been reported by theoretical calculations.The infrared and FT-Raman spectra of N⁴-acetylcytosine in the solid phase has been reported.

Purification Methods

If TLC or paper chromatography shows that it contains unacetylated cytosine, then reflux it in Ac2O for 4hours, cool at 3-4o for a few days, collect the crystals, wash them with cold H2O, then EtOH and dry at 100o. It is insoluble in EtOH and dissolves in H2O with difficulty, but crystallises in prisms from hot H2O. It is hydrolysed by 80% aqueous AcOH at 100o/1hour. [UV: Brown et al. J Chem Soc 2384 1956, Codington et al. J Am Chem Soc 80 5164 1958.] It forms an Hg salt [Fox et al. J Am Chem Soc 79 5060 1957]. [Beilstein 25 III/IV 3657.]