Uridine → 9-beta-D-arabinofuranosyl-2-amino-6-iodo-9H-purine

HRID 1736052

Reaction equation

HRID 1736052 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([I:11])[N:3]=1.C1C(=O)NC(=O)N([C@@H:20]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@@H:21]2[OH:28])C=1.[N-]=[N+]=[N-].[K+].[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[C@@H:20]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH2:1])=[N:3][C:4]=3[I:11])[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@@H:21]1[OH:28]

Participants

6

Reactant 4

HCID 6029Uridine2×HCID 18323Uracil ArabinosideHCID 61015752-Amino-6-iodopurineHCID 10290740Potassium azide

Product 1

HCID 538020069-beta-D-arabinofuranosyl-2-amino-6-iodo-9H-purineYield 11%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Conditions

Temperature
37 °C

Procedure

2-Amino-6-iodopurine (Sigma Chemicals, St. Louis. Mo.) (25.5 mmoles, 6.75 g) and uracil arabinoside (61.9 mmoles. 15.1 g) were combined in 0.31 liters of 10 mM potassium phosphate pH 6.9 with 0.02% potassium azide. Purified purine nucleoside phosphorylase (17000 units) and uridine phosphorylase (2000 units) were added and the solution stirred at 37° C. After 18 days an additional 5700 units of uridine phosphorylase were added. Fifty-seven days later the reaction was filtered and the flitrate chromatographed on a column containing XAD-2 resin (8×11 cm). The product was eluted with a step gradient of ethanol/water (v/v) as follows: 0.35 liter 10%; 1 liter 20%; 1 liter 50%; 0.2 liter 95%. Product-containing fractions were combined and the ethanol removed under vacuum. The residue was dissolved in 30% n-propanol/water (v/v) and chromatographed on a 7.5×90 cm column containing BioRad P-2 resin, This procedure yielded 1.1 g of 9-β-D-arabinofuranosyl-2-amino-6-iodo-9 H-purine as a 0.5 hydrate. NMR and mass spectrometry were consistent with the structure.

Workup

  1. filtrationFifty-seven days later the reaction was filtered
  2. customthe flitrate chromatographed on a column
  3. additioncontaining XAD-2 resin (8×11 cm)
  4. washThe product was eluted with a step gradient of ethanol/water (v/v)
  5. customthe ethanol removed under vacuum
  6. dissolutionThe residue was dissolved in 30% n-propanol/water (v/v)
  7. customchromatographed on a 7.5×90 cm column
  8. additioncontaining BioRad P-2 resin

Sources & evidence

ORD record
ord-1a1e16ea95be46ec8a9d3c0d42803855
Source dataset
uspto-grants-1996_07
Patent number
US05539098

Linked notes

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