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), 14␤-hydroxymorphine, 14␤-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14␤-hydroxydihydromorphinone) as substrate, the major transformation product was identified as oxymorphol (14␤-hydroxydihydromorphine). The identities of all these biological products were confirmed by mass spectrometry and 1 H nuclear magnetic resonance spectroscopy. This is the first report describing structural evidence for the biological synthesis of 14␤-hydroxymorphine and 14␤-hydroxymorphinone. These products have applications as intermediates in the synthesis of semisynthetic opiate drugs.

Transformations of codeine to important semisynthetic opiate derivatives by Pseudomonas putida m10

“…Reversed phase high performance liquid chromatography (HPLC) was performed as described in [10]. Thin-layer chromatography (TLC) was per-formed on silica plates with a mobile phase consisting of chloroform:methanol:ammonia (90:9:1 v/v/ v).…”

Microbial biotransformation of five pyrrolidinophenone‐type psychoactive substances in wastewater and a wastewater isolated Pseudomonas putida strain

“…[24,26] The P. putida strain M10, isolated from industrial waste liquors, was found to biotransform morphine and codeine through oxidation, reduction, and alkyl hydroxylation. [15,16,21,22] M10 catalyzes the formation of codeinone from codeine and grows on codeine as a sole carbon source. [17] Activated sludge batch studies have furthermore identified codeinone to be the main TP of codeine.…”

“…Individual P. putida strains have previously been used to catabolize aromatic and alkyl compounds . The P. putida strain M10, isolated from industrial waste liquors, was found to biotransform morphine and codeine through oxidation, reduction, and alkyl hydroxylation . M10 catalyzes the formation of codeinone from codeine and grows on codeine as a sole carbon source .…”

“…Furthermore, TPs are formed only in very small amounts. A further strategy to overcome such limitations could be to use isolated microbes mainly responsible for biotransformation and thus at least partially representative of the biotransformation processes in the biological systems. This could allow formation of TPs in higher amounts, easy standardization of incubation conditions, and shorter incubations times.…”

Biocatalysts screening of Papaver bracteatum flora for thebaine transformation to codeine and morphine

“…In addition to plant, microorganisms have ultimate potential to operate selective biochemical transformations (Rathbone and Bruce, 2002). There are many reports on the production of morphine alkaloids from fungi and bacteria including the genus Trametes (Boonstra et al, 2001;Bruce et al, 1990;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Long et al, 1995;Madyastha et al, 2000;Niknam et al, 2010), Cunninghamella (Abel et al, 2002;Asha and Vidyavathi, 2009;Boonstra et al, 2001;Bruce et al, 1990;Hartman et al, 1964;Kunz et al, 1985;Kyslíková et al, 2013;Niknam et al, 2010), Mucor piriformis (Kyslíková et al, 2013;Madyastha et al, 2000;Abel et al, 2002;Chaudhary et al, 2009), and Cylindrocarpon didymum (Boonstra et al, 2001;Rathbone and Bruce, 2002;Stabler et al, 2001); in a group of fungi and Arthrobacter sp. (Boonstra et al, 2001;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Long et al, 1995;Niknam et al, 2010), Pseudomonas testosteroni (Boonstra et al, 2001;Hailes and Bruce, 1993;Kunz et al, 1985;Kyslíková et al, 2013;Rathbone and Bruce, 2002), Pseudomonas putida (Boonstra et al, 2001;Bruce et al, 1990;Hailes and Bruce, 1993;…”