Uridine Monophosphate → Diuridine tetraphosphate tetraammonium salt

HRID 50555

反応式

HRID 50555 の反応式
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

参加物

7

反応物 4

HCID 6030Uridine MonophosphateHCID 6133Uridine 5'-triphosphateHCID 682631,1'-CarbonyldiimidazoleHCID 3724478Tributylammonium

生成物 1

HCID 131722997Diuridine tetraphosphate tetraammonium salt収率 30%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 7622Tributylamine溶媒2 回

反応条件

温度
50 °C

実験手順

Uridine 5′-monophosphate (Sigma, Milwaukee, 3.0 g, 9.26 mmol) was dissolved in dry DMF (10 mL) and tributylamine (Aldrich, 2 mL). The solution was evaporated in vacuo at 40° C. to an oil. The residue was dissolved in dry DMF (Aldrich, 8 mL) to form a solution. Carbonyldiimidazole (Aldrich, 1.65 g, 10.18 mmol) was added to this solution. The reaction was heated at 50° C. for one hour. Uridine 5′-triphosphate (Yamasa, 5.60 g, 10.18 mmol) prepared as the anhydrous tributylammonium salt in DMF (5 mL) and tributylamine (2 mL), as described in Example 3 below, was added to the reaction solution. The mixture was allowed to stir at 50° C. for three days when the solution was evaporated in vacuo to an oil, redissolved in water (5 mL) and purified by column (300×50 mm) chromatography (Sephadex DEAE-A25, 40-120μ, Aldrich, pre-swollen in 1.0 M NaHCO3 and washed with 2 column volumes of deionized H2O (H2O→0.3 M NH4HCO3 gradient). The pure fractions were concentrated in vacuo at 35° C., and H2O added and reevaporated 5 times to obtain diuridine tetraphosphate tetraammonium salt as a white solid (2.37 g, 30% yield): 92.11% pure by HPLC with the same retention time as the standard. In addition, the tetraammonium salt was analyzed by FABMS to give a mass of [C18H25N4O23P4 (M−H+)−: calculated 788.9860] 788.9857, confirming a parent formula of C18H26N4O23P4 for the free acid].

後処理

  1. customThe solution was evaporated in vacuo at 40° C. to an oil
  2. dissolutionThe residue was dissolved in dry DMF (Aldrich, 8 mL)
  3. customto form a solution
  4. additionwas added to the reaction solution
  5. customwas evaporated in vacuo to an oil
  6. dissolutionredissolved in water (5 mL)
  7. custompurified by column (300×50 mm) chromatography (Sephadex DEAE-A25, 40-120μ, Aldrich
  8. washpre-swollen in 1.0 M NaHCO3 and washed with 2 column volumes of deionized H2O (H2O→0.3 M NH4HCO3 gradient)
  9. concentrationThe pure fractions were concentrated in vacuo at 35° C.
  10. additionH2O added
  11. customreevaporated 5 times

出典と根拠

ORDレコード
ord-12af78c239e143439abb047a39605dce
出典データセット
uspto-grants-2004_03
特許番号
US06713458B1

関連ノート

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