Microbial models of mammalian metabolism. O-Dealkylation of 10,11-dimethoxyaporphine.
Microbial transformations of 10,11-dimethoxyaporphine were studied to determine the potential of microorganisms to produce monomethoxyaporphines. Ten microorganisms were identified as being capable of yielding apocodeine and/or isoapocodeine as the major metabolite in 24 and 20% yield, respectively. Cunninghamella blakesleeana (ATCC 9245) converted 10,11-dimethoxyaporphine quantitatively into isapocodeine. O-Dealkylation of this aporphine system is a facile microbial transformation, and the 10-methoxyl group is more susceptible to metabolic cleavage than the sterically hindered 11-methoxyl group. Selectivity in O-dealkylation may be accomplished with different microorganisms. This is the first report dealing with the microbial transformation of an aporphine system.
D001060:Aporphines / Q000378:metabolism*; D003640:Dealkylation; D005285:Fermentation; D008864:Microsporum / Q000378:metabolism; D003904:Mitosporic Fungi / Q000378:metabolism; D008954:Models, Biological; D009089:Mucor / Q000378:metabolism; D009090:Mucorales / Q000378:metabolism; D010407:Penicillium / Q000378:metabolism; D013302:Streptomyces / Q000378:metabolism
D001060:Aporphines