Deoxycytidine → 5-Hydroxy-2'-deoxycytidine

反応式

P([O:5][C@@H:6]1[C@@H:10]([CH2:11][O:12]P(O)(O)=O)[O:9][C@@H:8]([N:17]2[CH:24]=[C:23]([OH:25])[C:21]([NH2:22])=[N:20][C:18]2=[O:19])[CH2:7]1)(O)(O)=O.BrBr.[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)C1>O>[OH:25][C:23]1[C:21]([NH2:22])=[N:20][C:18](=[O:19])[N:17]([CH:24]=1)[C@@H:8]1[O:9][C@H:10]([CH2:11][OH:12])[C@@H:6]([OH:5])[CH2:7]1

参加物

実験手順

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).