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

HRID 1736051Notes

Reaction equation

HRID 1736051 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 80711,2-DimethoxyethaneSolventHCID 62657Potassium Phosphate, TribasicSolventHCID 10290740Potassium azideSolvent

Conditions

Temperature
35 °C

Procedure

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 flitrate 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 FP-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-9 H-purine that analyzed as a 1.5 hydrate. NMR and mass spectrometry were consistent with the structure.

Workup

  1. temperaturewith heating
  2. filtrationwas filtered
  3. customthe solvent removed under vacuum
  4. temperatureheated with steam
  5. filtrationfiltered
  6. customThe flitrate 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 FP-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

Sources & evidence

ORD record
ord-10bfbe7495054bc79970b163151ec72e
Source dataset
uspto-grants-1996_07
Patent number
US05539098

Reaction notes

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