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Adenine → 2'-Fluoro-2'-deoxyadenosine

HRID 37069
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 37069
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[F:11][C@@H:12]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][OH:19])[O:14][C@H:13]1N1C=CC(=O)NC1=O.[N-]=[N+]=[N-].[K+].[C@@H]1(N2C=C(C)C(=O)NC2=O)O[C@H](CO)[C@@H](O)C1>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[F:11][C@@H:12]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][OH:19])[O:14][C@H:13]1[N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 190AdenineHCID 5789ThymidineHCID 1508512'Fluoro-2'-deoxyuridineHCID 10290740Potassium azide2×

Produkt 1

HCID 1002532'-Fluoro-2'-deoxyadenosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62657
Potassium Phosphate, Tribasic
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

Adenine (Mann Research Laboratories, Inc., 0.8 g, 5.9 mmoles) and 1-(2-deoxy-2-fluoro-β-D-ribofuranosyl)uracil (0.4 g; 1.6 mmoles) which may be prepared according to J. F. Codington et al. (J. Org. Chem. 29:558, 1964) were suspended in 20 ml of 10 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/v) potassium azide. Thymidine phosphorylase (2,400 I.U.) and purine nucleoside phosphorylase (3,900 I.U.) (T. A. Krenitsky et al., Biochemistry 20:3615, 1981 and U.S. Pat. No. 4,381,344) were added and the suspension stirred at 37° C. On day 6, the reaction was diluted to 100 ml with 5 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/v) potassium azide. On day 17, the suspension was filtered and the filtrate was evaporated. The residue was suspended in warm water. The suspension was filtered and the filtrate applied to a 1.5×12 cm column of anion exchange resin (Bio-Rad AG1X2-hydroxide form). The product was eluted with water. Product containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilized to obtain the title compound that analyzed as a 0.6 hydrate.

Aufarbeitung

  1. addition4,381,344) were added
  2. waitOn day 6
  3. waitOn day 17
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated
  6. filtrationThe suspension was filtered
  7. washThe product was eluted with water
  8. additionProduct containing fractions
  9. customthe solvent removed under vacuum
  10. dissolutionThe residue was dissolved in water

Quellen und Nachweise

ORD-Eintrag
ord-492f07f3c31d4e92a53dd1a1c1b0a219
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05420115

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