Transformations of codeine to important semisynthetic opiate derivatives by Pseudomonas putida m10.
A biotransformation mixture which contained codeine and washed cells of Pseudomonas putida M10 gave rise to a number of transformation products that are of clinical importance which included hydrocodone, dihydrocodeine and 14beta-hydroxycodeine. Incubations with the same organism and codeinone gave rise to 14beta-hydroxycodeinone and 14beta-hydroxycodeine. Cell-free extracts and membrane fractions of P. putida M10 were shown to catalyse the 14beta-hydroxylation of codeinone. In addition, the potent analgesic oxycodone was shown to be produced from 14beta-hydroxycodeinone.
Lister
D L
DL
Institute of Biotechnology, University of Cambridge, Tennis Court Road, Cambridge, UK.
Kanungo
G
G
Rathbone
D A
DA
Bruce
N C
NC
D000429:Alcohol Oxidoreductases / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003061:Codeine / Q000031:analogs & derivatives / Q000378:metabolism*; D003470:Culture Media; D009682:Magnetic Resonance Spectroscopy; D010098:Oxycodone / Q000031:analogs & derivatives / Q000378:metabolism; D016958:Pseudomonas putida / Q000201:enzymology* / Q000254:growth & development
D003470:Culture Media; C046414:6-codeinone; C008000:hydroxycodeinone; D010098:Oxycodone; D000429:Alcohol Oxidoreductases; C045221:morphine 6-dehydrogenase; D003061:Codeine