Deoxycytidine → 5-Hydroxy-2'-deoxycytidine

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5-Hydroxydeoxycytidine is synthesized in a similar manner to the published procedure of Eaton et al. (Biochem. Biophys. Acta 319:281-287, 1973) for 5-hydroxydeoxycytidine-3',5'-diphosphate. Bromine is added to a cooled (0° C.) solution of 2'-deoxycytidine (available from Sigma Chemical Company) in water until the yellow color persists. The excess bromine is quenched with cyclohexene and 2,4,6-collidine is added. After 2 hours, the reaction mixture is washed with ether and evaporated to dryness under vacuum. The crude 5-hydroxydeoxycytidine is then purified by reversed-phase HPLC on an ULTRASPHERE C18 column (Phenomenex) using a linear gradient of 0%-20% B in A (solvent A: 0.1 M NH4OAc, solvent B: 50% CH3CN in 0.1 M NH4OAc).

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