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

HRID 21502
ノート
印刷プレビュー

反応式

HRID 21502 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
35 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07024dfe133a492982eb346fb71788a5
出典データセット
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05424295

反応ノート

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