Uridine Monophosphate → Uridine

Participants

Reaction Conditions

Reaction Steps

Uridine 5′-monosphate, tributylamine salt was prepared by dissolving uridine 5′-monophosphate, free acid (Sigma) (3.0 g) with tributylamine (2.0 mL) in DMF to make a 0.34M solution. An anhydrous DMF solution of uridine 5′-monophosphate tributylamine salt (5.6 ml, 1.89 mmol, 0.34 M) was added to a 10 ml round bottomed flask under N2 and carbonyldiimidazole (459 mg, 2.83 mmol) was added and the solution stirred at 25° C. for 30 min. A DMF solution of cytidine 5′-triphosphate tributylamine salt, prepared by treating the trisodium salt with Dowex 50H+ resin followed by tributylamine in DMF was added and the reaction mixture stirred at 65° C. for 3 h. The solution was evaporated in vacuo and purified two times by column chromatography (DEAE Sephadex; H2O→0.3M NH4HCO3 gradient). The pure fractions were concentrated in vacuo at 35° C., and H2O added and reevaporated ten times to obtain a white solid (203 mg): 1H NMR (D2O, TMS) δ4.1 (m, br, 6H), 4.2 (m, 4H), 5.8 (m, 3H), 5.95 (m, 1H), 7.7 (m, 2H); 31P NMR (D2O, H3PO4 std) δ−22.4 (m, 2P), −10.6 (m, 2P); Exact mass calc for C18H26N5O22P4 (M−H)=788.0020, found 787.9985.

Provenance & Evidence