Phosphoric Acid → guanosine-3'-diphosphate

HRID 848718Notes

Reaction equation

HRID 848718 reaction equation
[P:1]([O:5][C@@H:6]1[C@@H:10]([CH2:11][OH:12])[O:9][C@@H:8]([N:13]2[C:23]3[N:22]=[C:20]([NH2:21])[NH:19][C:17](=[O:18])[C:16]=3[N:15]=[CH:14]2)[C@@H:7]1[OH:24])(N)(=[O:3])[OH:2].[P:25](=[O:29])([OH:28])([OH:27])[OH:26]>N1C=CC=CC=1>[P:1]([O:5][C@@H:6]1[C@@H:10]([CH2:11][OH:12])[O:9][C@@H:8]([N:13]2[C:23]3[N:22]=[C:20]([NH2:21])[NH:19][C:17](=[O:18])[C:16]=3[N:15]=[CH:14]2)[C@@H:7]1[OH:24])([O:27][P:25]([OH:29])([OH:28])=[O:26])(=[O:3])[OH:2]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 136181547HCID 136181547, compound

Product 1

HCID 135566255guanosine-3'-diphosphate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.35 millimoles of the guanosine-3'-monophosphoramidate and 1.5 millimoles of inorganic phosphoric acid was dissolved in 2.0 ml of dried pyridine, the solution was left to stand at room temperature for a period of 3 or 4 days, the undissolved matter was filtered off, and the filtrate was concentrated under vacuum to remove the pyridine. The residue was dissolved in 25 ml of an aqueous solution that contained 1 g of sodium acetate, the solution was adjusted to a pH of 7.0 with sodium hydroxide, and washed five times with ether twice the volume of the solution to remove the guanidium salt. The solution was then passed through a column of Dowex 2 (Cl- type: manufactured by Dow Chemical Co.) to remove the unreacted guanosine-3'-monophosphoramidate. The solution was treated with lithium hydroxide to bring its pH to 6.5, concentrated under vacuum, the residue was dissolved in 25 ml of methanol, to which was added 200 ml of acetone to precipitate the crystal of a lithium salt of guanosine-3'-diphosphate. The crystal was passed through a column of Dowex 50 (H+ type) for desalting. The eluate was collected, concentrated under vacuum, and the residue was lyophilized to give guanosine-3'-diphosphate.

Workup

  1. waitthe solution was left
  2. filtrationthe undissolved matter was filtered off
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto remove the pyridine
  5. dissolutionThe residue was dissolved in 25 ml of an aqueous solution that
  6. washwashed five times with ether twice the volume of the solution
  7. customto remove the guanidium salt
  8. customto remove the unreacted guanosine-3'-monophosphoramidate
  9. additionThe solution was treated with lithium hydroxide
  10. concentrationconcentrated under vacuum
  11. dissolutionthe residue was dissolved in 25 ml of methanol, to which
  12. additionwas added 200 ml of acetone
  13. customto precipitate the crystal of a lithium salt of guanosine-3'-diphosphate
  14. customThe eluate was collected
  15. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3caac77c0ec54f868985e6376edf7a88
Source dataset
uspto-grants-1981_10
Patent number
US04297347

Reaction notes

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