Reaktion #49779

Reaktionsgleichung

uridine

2-Amino-6-iodopurine

uracil arabinoside

uridine

potassium azide

→

9-β-D-arabinofuranosyl-2-amino-6-iodo-9H-purine

Ausbeute 11.0%

Lösungsmittel

potassium phosphate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationFifty-seven days later the reaction was filtered
2. 2
   Sonstigethe filtrate chromatographed on a column
3. 3
   workup.ADDITIONcontaining XAD-2 resin (8×11 cm)
4. 4
   WaschenThe product was eluted with a step gradient of ethanol/water (v/v)
5. 5
   Sonstigethe ethanol removed under vacuum
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 30% n-propanol/water (v/v)
7. 7
   Sonstigechromatographed on a 7.5×90 cm column
8. 8
   workup.ADDITIONcontaining BioRad P-2 resin

Vorschrift

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 filtrate 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-9H-purine as a 0.5 hydrate. NMR and mass spectrometry were consistent with the structure. Anal. Calcd. for C10H12IN5O4.05H2O: Calcd: C, 29.87; H, 3.26; N, 17.41. Found: C, 29.86; H, 3.29; N, 17.39.

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