HCID 178508223, compound → Guanosine

HRID 1032458Notes

Reaction equation

HRID 1032458 reaction equation
[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C@@H]1(N2C3N=CN=C(O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O.[C@@H]1(N2C3N=CN=C(O)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1O>>[C@@H:1]1([N:10]2[C:20]3[N:19]=[CH:17][N:16]=[C:14]([OH:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 178508223HCID 178508223, compoundHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 2

HCID 135398635GuanosineHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Procedure

Each of 24.9 g, 35.2 g and 46.9 g portions of mixed crystals composed of 21.1% inosine, 48.9% guanosine and 28.0% water were weighed out and placed in 300 ml round bottom flasks. Then, the flasks were placed in a thermostat bath at 10° C. Into each flask was added 93 ml, 90 ml or 86 ml of water (10° C.) to obtain a suspension (pH=5.7) which were stirred for 2 hours and centrifuged (10,000 G for 10 min.). The supernatant as filtered through Milipore filter (0.45 μ) and the amounts of inosine and guanosine contained in the filtrate were determined. FIG. 1 shows the results of determination of the concentration of each slurry when the mixed crystals were suspended and the amounts of guanosine/inosine (%) and inosine (mg/ml) contained in the supernatant. As seen from this figure, at any slurry concentration, guanosine/inosine (%) in the supernatant is not less than 5% and the amount of residual guanosine is still relatively high. Further, the drawing shows that the concentration of inosine is as low as about 5 mg/ml. Therefore, in order to obtain inosine substantially free from guanosine efficiently, it is apparent that this process would not be satisfactory.

Workup

  1. customcentrifuged (10,000 G for 10 min.)
  2. filtrationThe supernatant as filtered through Milipore
  3. filtrationfilter (0.45 μ)
  4. customresults of determination of the concentration of each slurry when the mixed crystals
  5. concentrationAs seen from this figure, at any slurry concentration, guanosine/inosine (%) in the supernatant

Sources & evidence

ORD record
ord-a171a62eaad94a4e88eb13a69afc3362
Source dataset
uspto-grants-1990_09
Patent number
US04958017

Reaction notes

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