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Transformations of morphine alkaloids by Pseudomonas putida M10
M T Long1, A M Hailes, G W Kirby
1Institute of Biotechnology, University of Cambridge, United Kingdom.
Applied and Environmental Microbiology
|October 1, 1995
Summary
Pseudomonas putida M10 transforms morphine into several products, including 14 beta-hydroxymorphine. This study provides the first structural evidence for the biological synthesis of these compounds, which are key intermediates for semisynthetic opiate drugs.
Area of Science:
- Microbiology
- Medicinal Chemistry
- Biocatalysis
Background:
- Opiate drugs are widely used for pain management.
- The microbial transformation of opiates can yield novel compounds.
- Understanding these biotransformations is crucial for drug development.
Purpose of the Study:
- To investigate the microbial oxidation of morphine by Pseudomonas putida M10.
- To identify and structurally characterize the resulting transformation products.
- To establish the biological synthesis pathways for key opiate intermediates.
Main Methods:
- Washed-cell incubations of Pseudomonas putida M10 with morphine and oxymorphone.
- Identification of transformation products using mass spectrometry.
- Structural elucidation using 1H nuclear magnetic resonance (NMR) spectroscopy.
Main Results:
- Morphine oxidation yielded hydromorphone, 14 beta-hydroxymorphine, 14 beta-hydroxymorphinone, and dihydromorphine.
- Oxymorphone incubation primarily produced oxymorphol (14 beta-hydroxydihydromorphine).
- This research presents the first structural evidence for the microbial synthesis of 14 beta-hydroxymorphine and 14 beta-hydroxymorphinone.
Conclusions:
- Pseudomonas putida M10 efficiently transforms morphine into valuable opiate derivatives.
- The identified products, 14 beta-hydroxymorphine and 14 beta-hydroxymorphinone, are significant intermediates.
- These findings support the use of microbial biotransformation in the synthesis of semisynthetic opiate drugs.