Thymidine → 2-Amino-2'-deoxy-2'-fluoroadenosine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

2,6-Diaminopurine (Pacific Chemical Laboratories, 0.8 g, 4.8 mmoles) and 1-(2-deoxy-2-fluoro-β-D-ribofuranosyl)uracil (0.4 g, 1.6 mmoles) which may be prepared according to J. F. Codington et al. (J. Org. Chem. 29:558, 1964) were suspended in 50 ml of 5 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/w) potassium azide. Thymidine phosphorylase (3,850 I.U.) and purine nucleoside phosphorylase (3,760 I.U.) (T. A. Krenitsky et al., Biochemistry 20:3615, 1981 and U.S. Pat. No. 4,381,344) were added and the suspension stirred at 37° C. On day 12, the reaction was filtered. The filtrate was applied to a 1.5×15 cm column of anion exchange resin (Bio-Rad AG1X2-hydroxide form). After washing the column with water/methanol (7/3), the product was eluted with water/methanol (1/1). Product containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilized to obtain title compound that analyzed as a 1.2 hydrate.

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