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

HRID 1736053Notes

Reaction equation

HRID 1736053 reaction equation
[N:1]1([C:6]2[N:14]=[CH:13][N:12]=[C:11]3[C:7]=2[NH:8][CH:9]=[N:10]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)NC(=O)N([C@@H:23]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@@H:24]2[OH:31])C=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>>[C@@H:23]1([N:10]2[CH:9]=[N:8][C:7]3[C:11]2=[N:12][CH:13]=[N:14][C:6]=3[N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@@H:24]1[OH:31]

Participants

5

Reactant 4

HCID 6029UridineHCID 18323Uracil ArabinosideHCID 62657Potassium Phosphate, TribasicHCID 7566906-(pyrrolidin-1-yl)-9H-purine

Product 1

HCID 541884899-beta-D-arabinofuranosyl-6-pyrrolidino-9H-purineYield 68.6%

Conditions

Temperature
35 °C

Procedure

6-Pyrrolidinopurine (Sigma Chemical Co., St. Louis, Mo.) (2.6 mmoles), 0.5 g, and uracil arabinoside (5.29 mmoles, 1.29 g) were suspended in 100 ml of a 10 mM potassium phosphate 0.04% potassium azide solution with a pH of 7.4. Purified uridine phosphorylase (6000 I.U.) and purine nucleoside phosphorylase (8400 I.U.) (Krenitsky, T. A., et al. Biochemistry, 20, 3615 (1981) and U.S. Pat. No. 4,381,344) were added and the suspension stirred at 35° C. Twenty days later the reaction was filtered and the filtrate chromatographed on a column containing Dowex-I-hydroxide resin (2.5×8 cm). The product was eluted from the column with 90% methanol/water (v/v). Fractions containing product were combined and the solvent removed under vacuum. The residue was dissolved in 50 ml of 30% n-propanol and water (v/v) and chromatographed on a BioRad P-2 column (5×90 cm). The product was eluted with 30% n-propanol/water (v/v). Product-containing fractions were combined and the solvent was removed under vacuum yielding 0.573 g of 9-β-D-arabinofuranosyl-6-pyrrolidino-9 H-purine. NMR and mass spectrometry were consistent with the structure.

Workup

  1. addition4,381,344) were added
  2. filtrationTwenty days later the reaction was filtered
  3. customthe filtrate chromatographed on a column
  4. additioncontaining Dowex-I-hydroxide resin (2.5×8 cm)
  5. washThe product was eluted from the column with 90% methanol/water (v/v)
  6. additionFractions containing product
  7. customthe solvent removed under vacuum
  8. dissolutionThe residue was dissolved in 50 ml of 30% n-propanol
  9. customwater (v/v) and chromatographed on a BioRad P-2 column (5×90 cm)
  10. washThe product was eluted with 30% n-propanol/water (v/v)
  11. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5b85efe368104d799d1c50f79e1f3e32
Source dataset
uspto-grants-1996_07
Patent number
US05539098

Reaction notes

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