Pseudoephedrine → (-)-Pseudoephedrine

HRID 2308166Notes

Reaction equation

HRID 2308166 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[CH3:21][C@H:22]([NH:31][CH3:32])[C@@H:23]([OH:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1>>[CH3:21][C@@H:22]([NH:31][CH3:32])[C@H:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Conditions

Temperature
28 °C

Procedure

Coprinus rhizophorus IFO 30197 was inoculated to a medium containing 1% glucose, 0.5% peptone and 0.3% yeast extract, and culturing was aerobically carried out at 30° C. for 48 hours. After this cultured solution (5 ml) was centrifuged to give bacterial cells, the cells were dried in the air and the resulting dried bacterial cells were suspended in 1 ml of 0.05 M Tris hydrochloric acid buffer (pH 7.5). To this were added glucose (50 mg), glucose dehydrogenase (0.2 mg), NADP (0.6 mg), NAD (0.6 mg) and dl-2-methylamino-1-phenyl-1-propanone hydrochloride (10 mg). Reaction was allowed to take place by carrying out reciprocation-shaking at 28° C. and at 300 rpm for 48 hours. The reaction solution was analyzed on HPLC (Column Sumichiral AGP manufactured by Sumika Chemical Analysis Service; diameter of 4 mm; length of 150 mm; 0.03 M sodium phosphate buffer; pH 7.0; flow rate of 0.5 ml/min; detection wavelength at UV 220 nm). The produced amounts and the optical activities of pseudoephedrine were determined. Consequently, only l-pseudoephedrine was obtained selectively, as shown in Table 6.

Workup

  1. extractionextract
  2. customto give bacterial cells
  3. customthe cells were dried in the air
  4. customthe resulting dried bacterial cells
  5. additionTo this were added glucose (50 mg), glucose dehydrogenase (0.2 mg), NADP (0.6 mg), NAD (0.6 mg)
  6. customReaction

Sources & evidence

ORD record
ord-c4584cfc9b044935bf7e852eca4ee669
Source dataset
uspto-grants-2004_12
Patent number
US06835559B2

Reaction notes

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