(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Pseudoephedrine

Participants

Reaction Steps

Mycobacterium smegmatis IAM-12065 was inoculated to a medium containing 1% glucose, 0.5% peptone, and 0.3% yeast extract, and shake-culturing was aerobically carried out at 30° C. for 48 hours. After the cultured solution (1 l) was centrifuged to give bacterial cells, the cells was suspended in 50 ml of water, and after addition of dl-2-methylamino-1-phenyl-1-propanone hydrochloride (0.5 g), reciprocation-shaking was carried out at 30° C. and at 150 rpm. One hundred hours after the start of shaking, 7.0 g/l of d-pseudoephedrine was produced in the reaction solution. After the reaction solution was centrifuged to remove the bacterial cells, the pH was adjusted to 12 or greater by addition of sodium hydroxide. Methylene chloride (100 ml) was added to this reaction solution and the reaction product was extracted. The solvent was removed, hydrochloric acid was added, and then concentration to dryness yielded a hydrochloride salt. The hydrochloride salt was dissolved by addition of ethanol and further addition of ether crystallized the reaction product. Consequently, d-pseudoephedrine hydrochloride was obtained. The resulting d-pseudoephedrine crystals (0.32 g) were 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 light wavelength at UV 220 nm) and the optical activity was found to be 100%.

Provenance & Evidence