反応 #49786

反応方程式

6-n-Propoxypurine

uracil arabinoside

uridine

→

9-β-D -arabinofuranosyl-6-n-propoxy-9H-purine

収率 43.6%

溶媒

n-propanol

potassium phosphate

反応条件

後処理

1. 1
   ろ過The reaction was filtered after 58 days
2. 2
   その他The resulting precipitate was collected by centrifugation
3. 3
   workup.DISSOLUTIONdissolved in 30% n-propanol/water (v/v)
4. 4
   その他chromatographed on a column of Dowex-1-formate resin (2.5×5 cm)
5. 5
   洗浄The column was eluted with 30% n-propanol/water (v/v) and fractions
6. 6
   workup.ADDITIONcontaining product
7. 7
   その他solvent removed in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in n-propanol
9. 9
   その他chromatographed on a column
10. 10
    workup.ADDITIONcontaining BioRad P-2 (5×90 cm)
11. 11
    洗浄The column was eluted with 30% n-propanol/water (v/v)
12. 12
    その他after removing the solvent under vacuum the residue
13. 13
    workup.DISSOLUTIONwas dissolved in water
14. 14
    その他chromatographed on a column
15. 15
    workup.ADDITIONcontaining BioRad P-2 (5×90 cm)
16. 16
    洗浄The column was eluted with water
17. 17
    workup.ADDITIONProduct containing fractions

実験手順

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.

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