Uridine → 9-beta-D-arabinofuranosyl-6-iodo-9H-purine

HRID 21500

反応式

HRID 21500 の反応式
[I:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C1C(=O)NC(=O)N([C@@H:19]2[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@@H:20]2[OH:27])C=1.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>COCCOC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N-]=[N+]=[N-].[K+]>[C@@H:19]1([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][CH:9]=[N:10][C:2]=3[I:1])[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@@H:20]1[OH:27]

参加物

7

反応物 3

HCID 6029Uridine2 回HCID 18323Uracil ArabinosideHCID 54630676-Iodo-9H-purine

生成物 1

HCID 543632589-beta-D-arabinofuranosyl-6-iodo-9H-purine収率 16.7%

試薬・触媒・溶媒 3

HCID 80711,2-Dimethoxyethane溶媒HCID 62657Potassium Phosphate, Tribasic溶媒HCID 10290740Potassium azide溶媒

反応条件

温度
35 °C

実験手順

6-Iodopurine (Sigma Chemical Co. St. Louis, Mo.) (4 mmoles, 1 g) was dissolved in 15 ml of 1,2-dimethoxyethane with heating. Fifty milliliters of a uracil arabinoside solution (10.1 mmoles) in 10 mM potassium phosphate, 0.04% potassium azide solution, pH of 7.4, were added. Purified uridine phosphorylase (6800 I.U.) and purine nucleoside phosphorylase (12000 I.U.) were added and the reaction stirred at 35° C. After 21 days an additional 4800 units of uridine phosphorylase and 20000 units of purine nucleoside phosphorylase were added. Ninety days later the reaction was filtered and the solvent removed under vacuum. The residue was suspended in 100 ml of water, heated with steam, and then filtered. The filtrate was chromatographed on a column containing XAD-2 resin (5×35 cm), eluting with 2 liters of water followed by 2 liters ethanol. Fractions containing product were combined and the solvent removed under vacuum. The residue was dissolved in 30% n-propanol/water (v/v) and chromatographed on a column containing BioRad P-2 (5×90 cm). The product was eluted with 30% n-propanol/water (v/v). Product-containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in 30% n-propanol/water (v/v) and chromatographed on a Sephadex G-10 column (5×90 cm). This column was eluted with 30% n-propanol/water (v/v). Product-containing fractions were combined and after removing the solvent under vacuum, yielded 0.253 g of 9-β-D-arabinofuranosyl-6-iodo-9H-purine that analyzed as a 1.5 hydrate. NMR and mass spectrometry were consistent with the structure. Anal. Calcd. for C10H11IN4O4.1.5 H2O: Calcd: C, 29.65; H, 3.48; N, 13.83; I, 31.32. Found: C, 29.43; H, 3.53; N, 13.66; I, 31.20.

後処理

  1. temperaturewith heating
  2. filtrationNinety days later the reaction was filtered
  3. customthe solvent removed under vacuum
  4. temperatureheated with steam
  5. filtrationfiltered
  6. customThe filtrate was chromatographed on a column
  7. additioncontaining XAD-2 resin (5×35 cm)
  8. washeluting with 2 liters of water
  9. additionFractions containing product
  10. customthe solvent removed under vacuum
  11. dissolutionThe residue was dissolved in 30% n-propanol/water (v/v)
  12. customchromatographed on a column
  13. additioncontaining BioRad P-2 (5×90 cm)
  14. washThe product was eluted with 30% n-propanol/water (v/v)
  15. customthe solvent removed under vacuum
  16. dissolutionThe residue was dissolved in 30% n-propanol/water (v/v)
  17. customchromatographed on a Sephadex G-10 column (5×90 cm)
  18. washThis column was eluted with 30% n-propanol/water (v/v)
  19. customafter removing the solvent under vacuum

出典と根拠

ORDレコード
ord-ee80fc64f34e43ffa5a846721ffebb29
出典データセット
uspto-grants-1995_06
特許番号
US05424295

関連ノート

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