Klot
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biosyntesys hydrocodone from codeine
m was found this artilcle
Transformations of Morphine Alkaloids by Pseudomonas putida M10
The oxidation of morphine by washed-cell incubations of Pseudomonas putida M10 gave rise to a large
number of transformation products including hydromorphone (dihydromorphinone), 14b-hydroxymorphine,
14b-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14b-hydroxydihydromorphinone)
as substrate, the major transformation product was identified as oxymorphol (14b-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 14b-hydroxymorphine and 14b-hydroxymorphinone. These products have applications
as intermediates in the synthesis of semisynthetic opiate drugs.
http://microscopiumd.mofile.com/5965936162331500/56667993042...
Biological Synthesis of the Analgesic Hydromorphone, an
Intermediate in the Metabolism of Morphine, by
Pseudomonas putida M10
The morphine alkaloid hydromorphone (dihydromorphinone) was identified as an intermediary metabolite
in the degradation of morphine by Pseudomonas putida M10. A constitutive NADH-dependent morphinone
reductase capable of catalyzing the reduction of the 7,8-unsaturated bond of morphinone and codeinone,
yielding hydromorphone and hydrocodone, respectively, was shown to be present in cell extracts. The
structures have been identified by 'H nuclear magnetic resonance and mass spectrometry. Morphinone
reductase has been partially purified by anion-exchange and gel filtration chromatography. This enzyme has
potential applications as a biocatalyst for the synthesis of the highly potent analgesic hydromorphone and the
antitussive hydrocodone.
http://microscopiumd.mofile.com/1401376467634022/72423339024...
FEMS Microbiology Letters
Volume 181, Issue 1 , 1 December 1999, Pages 137-144
Transformations of codeine to important semisynthetic opiate derivatives by Pseudomonas putida m10
Abstract
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 14β-hydroxycodeine. Incubations with the same organism and codeinone
gave rise to 14β-hydroxycodeinone and 14β-hydroxycodeine. Cell-free extracts and membrane fractions of P. putida M10 were shown to catalyse
the 14β-hydroxylation of codeinone. In addition, the potent analgesic oxycodone was shown to be produced from 14β-hydroxycodeinone.
Q: May are barm works in this situation ?
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unionised
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I think you need to clarify that question.
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sparkgap
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Apparently, this means you can try adding opium dross to a flourishing culture of P. putida and voila, Oxycontin by the heap!
Anyway, question. The only Pseudomonas species I'm knowledgeable in is the (really nasty) P. aeruginosa. I'd wonder if the
morphine-converting species is as abundant as its more common kin? Wouldn't this organism require special conditions as well for cultivation?
sparky (~_~)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
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