4-Aminobenzoic Acid → Trisodium Phosphate

HRID 1374513Notes

Reaction equation

HRID 1374513 reaction equation
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[P:24]([O-:28])([OH:27])([OH:26])=[O:25].[K+].P([O-])([O-])(O)=O.[K+].[K+].NC1C=CC(C(O)=O)=CC=1.P([O-])([O-])([O-])=O.[Na+:52].[Na+].[Na+].Cl.[CH3:56][NH:57][CH:58]([CH3:67])[C:59]([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:60].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[P:24]([O-:28])([O-:27])([O-:26])=[O:25].[Na+:52].[Na+:52].[Na+:52].[CH3:67][C@H:58]([NH:57][CH3:56])[C@@H:59]([OH:60])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

9

Conditions

Temperature
30 °C

Procedure

Rhodococcus erythropolis MAK-34 strain was planted in 5 ml of a medium at pH 7.0 containing 1.0% of saccharose, 0.5% of corn steep liquor, 0.1% of potassium dihydrogenphosphate, 0.3% of dipotassium hydrogenphosphate, 0.01% of p-aminobenzoic acid, and 0.1% of various kinds of inducers, and was shaking-cultured at 30° C. for 48 hours. The culture medium was centrifuged, so as to yield the cells, which were then put into a test tube, and were suspended with 1.0 ml of 0.2-M sodium phosphate buffer solution (pH 7.0) added thereto. With 10 mg of dl-2-methylaminopropiophenone hydrochloride and 20 mg of glucose added thereto, the suspension was shaken at 30° C. for 16 hours, so as to effect a reaction. After the reaction was completed, the reaction mixture was centrifuged, so as to remove the cells, whereas the supernatant was subjected to HPLC (μBondapakphenyl, manufactured by Waters Corporation, with a diameter of 4 mm, a length of 300 mm, an eluent of 0.05 M sodium phosphate buffer solution (containing 7% of acetonitrile, at pH 6.5), a flow rate of 0.8 mL/min, and a detection wavelength of 220 nm), whereby an optically active pseudoephedrine was obtained. The amount of production thereof was remarkably greater than that in the case with no inducer addition as shown in Table 7.

Workup

  1. customso as to yield the cells, which
  2. customwere then put into a test tube
  3. additionadded
  4. stirringthe suspension was shaken at 30° C. for 16 hours
  5. customa reaction
  6. customso as to remove the cells

Sources & evidence

ORD record
ord-59daf1530be243d08041acb686ecd349
Source dataset
uspto-grants-2007_01
Patent number
US07166452B2

Reaction notes

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