Uridine → 2-Hydroxymethyl-5-(6-propoxy-purin-9-yl)-tetrahydro-furan-3,4-diol

HRID 21508

Reaktionsgleichung

Reaktionsgleichung von HRID 21508
[CH2:1]([O:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2)[CH2:2][CH3:3].C1C(=O)NC(=O)N([C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@@H:23]2[OH:30])C=1.[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(O)CC>[C@@H:22]1([N:9]2[CH:8]=[N:7][C:6]3[C:10]2=[N:11][CH:12]=[N:13][C:5]=3[O:4][CH2:1][CH2:2][CH3:3])[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@@H:23]1[OH:30]

Komponenten

6

Edukt 3

HCID 6029UridineHCID 18323Uracil ArabinosideHCID 794516-Propoxy-1H-purine

Produkt 1

HCID 30111532-Hydroxymethyl-5-(6-propoxy-purin-9-yl)-tetrahydro-furan-3,4-diolAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10311-PropanolLösungsmittelHCID 62657Potassium Phosphate, TribasicLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

6-n-Propoxypurine (5.6 mmoles, 1 g, Sigma Chemicals, St. Louis Mo.) was combined with 545 ml of a uracil arabinoside solution (10.1 mmoles) in 10 mM potassium phosphate and 7% n-propanol (v/v). Purified uridine phosphorylase (680 I.U.) and purine nucleoside phosphorylase (12000 I.U.) were added and the reaction stirred at 35° C. The reaction was filtered after 58 days and the filtrate stored at 3° C. for 20 hours. The resulting precipitate was collected by centrifugation, dissolved in 30% n-propanol/water (v/v), and chromatographed on a column of Dowex-1-formate resin (2.5×5 cm) after adjusting the pH to 10.5 with concentrated ammonium hydroxide. The column was eluted with 30% n-propanol/water (v/v) and fractions containing product were combined and solvent removed in vacuo. The residue was dissolved in n-propanol and chromatographed on a column containing BioRad P-2 (5×90 cm). The column was eluted with 30% n-propanol/water (v/v). Product-containing fractions were combined and after removing the solvent under vacuum the residue was dissolved in water and chromatographed on a column containing BioRad P-2 (5×90 cm). The column was eluted with water. Product containing fractions were combined and after lyophilization, yielded 0.758 g of 9-β-D -arabinofuranosyl-6-n-propoxy-9H-purine that analyzed as a monohydrate. NMR and mass spectrometry were consistent with the structure. Anal. Calcd. for C13H18N4O5.H2O: Calcd: C, 47.56; H, 6.14; N, 17.06. Found: C, 47.63; H, 6.13; N, 17.11.

Aufarbeitung

  1. filtrationThe reaction was filtered after 58 days
  2. customThe resulting precipitate was collected by centrifugation
  3. dissolutiondissolved in 30% n-propanol/water (v/v)
  4. customchromatographed on a column of Dowex-1-formate resin (2.5×5 cm)
  5. washThe column was eluted with 30% n-propanol/water (v/v) and fractions
  6. additioncontaining product
  7. customsolvent removed in vacuo
  8. dissolutionThe residue was dissolved in n-propanol
  9. customchromatographed on a column
  10. additioncontaining BioRad P-2 (5×90 cm)
  11. washThe column was eluted with 30% n-propanol/water (v/v)
  12. customafter removing the solvent under vacuum the residue
  13. dissolutionwas dissolved in water
  14. customchromatographed on a column
  15. additioncontaining BioRad P-2 (5×90 cm)
  16. washThe column was eluted with water
  17. additionProduct containing fractions

Quellen und Nachweise

ORD-Eintrag
ord-3c21586c1185429fb486281e9d63b50e
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424295

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