Hydroxylation and Further Oxidation of Δ 9 -Tetrahydrocannabinol by Alkane-Degrading Bacteria
| Autor: | Hassan Rashidi, Robert Verpoorte, Frank van der Kooy, Wouter A. Duetz, Muhammad Akhtar |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
food.ingredient
Stereochemistry Carboxylic acid Gordonia Hydroxylation Applied Microbiology and Biotechnology Mass Spectrometry chemistry.chemical_compound food Biotransformation Alkanes Organic chemistry Dronabinol Methylene Alkyl chemistry.chemical_classification Bacteria Ecology biology biology.organism_classification Models Chemical chemistry Oxidation-Reduction Rhodococcus Two-dimensional nuclear magnetic resonance spectroscopy Food Science Biotechnology |
| Zdroj: | Applied and Environmental Microbiology. 75:7135-7141 |
| ISSN: | 1098-5336 0099-2240 |
| DOI: | 10.1128/aem.01277-09 |
| Popis: | The microbial biotransformation of Δ 9 -tetrahydrocannabinol was investigated using a collection of 206 alkane-degrading strains. Fifteen percent of these strains, mainly gram-positive strains from the genera Rhodococcus , Mycobacterium , Gordonia , and Dietzia , yielded more-polar derivatives. Eight derivatives were produced on a mg scale, isolated, and purified, and their chemical structures were elucidated with the use of liquid chromatography-mass spectrometry, 1 H-nuclear magnetic resonance ( 1 H-NMR), and two-dimensional NMR ( 1 H- 1 H correlation spectroscopy and heteronuclear multiple bond coherence). All eight biotransformation products possessed modified alkyl chains, with hydroxy, carboxy, and ester functionalities. In a number of strains, β-oxidation of the initially formed C 5 carboxylic acid led to the formation of a carboxylic acid lacking two methylene groups. |
| Databáze: | OpenAIRE |
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