Pyrophosphoric acid → Guanosine Monophosphate

HRID 276749

Reaction equation

HRID 276749 reaction equation
[P:1]([O:5]P(O)(O)=O)([OH:4])([OH:3])=[O:2].[C@@H:10]1([N:19]2[C:28]3[N:27]=[CH:26][N:25]=[C:23]([OH:24])[C:22]=3[N:21]=[CH:20]2)[O:18][C@H:15]([CH2:16]O)[C@@H:13]([OH:14])[C@H:11]1[OH:12].[C@@H:29]1([N:38]2[C:48]3[N:47]=[C:45]([NH2:46])[NH:44][C:42](=[O:43])[C:41]=3[N:40]=[CH:39]2)[O:37][C@H:34]([CH2:35][OH:36])[C@@H:32]([OH:33])[C@H:30]1[OH:31]>C([O-])(=O)C>[C@@H:10]1([N:19]2[C:28]3[N:27]=[CH:26][N:25]=[C:23]([OH:24])[C:22]=3[N:21]=[CH:20]2)[O:18][C@H:15]([CH2:16][O:5][P:1]([OH:3])([OH:4])=[O:2])[C@@H:13]([OH:14])[C@H:11]1[OH:12].[C@@H:29]1([N:38]2[C:48]3[N:47]=[C:45]([NH2:46])[NH:44][C:42](=[O:43])[C:41]=3[N:40]=[CH:39]2)[O:37][C@H:34]([CH2:35][O:36][P:1]([OH:4])([OH:3])=[O:2])[C@@H:32]([OH:33])[C@H:30]1[OH:31]

Participants

6

Reactant 3

HCID 1023Pyrophosphoric acidHCID 135398635GuanosineHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 2

HCID 135398631Guanosine MonophosphateHCID 178527090HCID 178527090, compound

Reagents, catalysts & solvents 1

HCID 175AcetateSolvent

Procedure

Pyrophosphoric acid (15 g/dl) and 8 g/dl of inosine or guanosine were dissolved in an acetate buffer (pH 4.0). To this was added E. coli JM109 strain having introduced therein each mutant acid phosphatase gene such that the concentration reached 100 mg/dl in terms of the dry cell weight. The reaction was conducted at 50° C. for 9 hours while maintaining the pH at 4.0, and the amount of 5′-inosinic acid or 5′-guanylic acid formed was measured. The results are shown in Table 17. The nucleoside phosphate ester formed was only a nucleoside-5′-phosphate ester, and the production of a nucleoside-2′-phosphate ester and a nucleoside-3′-phosphate ester as by-products was not observed at all. The reaction was also conducted at 30° C. for 12 hours using E. coli JM109/pEPI380 strain as a control. The results are also shown in Table 17.

Workup

  1. additionTo this was added E
  2. additionstrain having introduced
  3. concentrationeach mutant acid phosphatase gene such that the concentration
  4. temperaturewhile maintaining the pH at 4.0

Sources & evidence

ORD record
ord-21e6e5ab5fcc4010bb668be326a5c704
Source dataset
uspto-grants-2002_03
Patent number
US06355472B2

Linked notes

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