Transformations of morphine alkaloids by Pseudomonas putida M10

Abstract

The oxidation of morphine by washed-cell incubations of Pseudomonas putida M10 gave rise to a large number of transformation products including hydromorphone (dihydromorphinone), 14β-hydroxymorphine, 14β- hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14β-hydroxydihydromorphinone) as substrate, the major transformation product was identified as oxymorphol (14β- hydroxydihydromorphine). The identities of all these biological products were confirmed by mass spectrometry and 1H nuclear magnetic resonance spectroscopy. This is the first report describing structural evidence for the biological synthesis of 14β-hydroxymorphine and 14β-hydroxymorphinone. These products have applications as intermediates in the synthesis of semisynthetic opiate drugs.