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

HRID 21502

반응식

HRID 21502 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

반응 조건

온도
35 °C

실험 절차

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-1-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-9H-purine. NMR and mass spectrometry were consistent with the structure. Anal. Calcd. for C14H19N5O4 : Calcd: C, 52.33; H, 5.96 N, 21.79. Found: C, 52.60; H, 6.09; N, 21.51.

후처리

  1. addition4,381,344) were added
  2. filtrationTwenty days later the reaction was filtered
  3. customthe filtrate chromatographed on a column
  4. additioncontaining Dowex-1-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

출처 및 근거

ORD 기록
ord-07024dfe133a492982eb346fb71788a5
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424295

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