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....
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| Veröffentlicht in: | Journal of medicinal chemistry 1975-08, Vol.18 (8), p.791-794 |
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| container_title | Journal of medicinal chemistry |
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| creator | Rosazza, J. P Stocklinski, A. W Gustafson, M. A Adrian, J Smith, R. V |
| description | 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. |
| doi_str_mv | 10.1021/jm00242a006 |
| format | Article |
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Selectivity in O-dealkylation may be accomplished with different microorganisms. 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Selectivity in O-dealkylation may be accomplished with different microorganisms. This is the first report dealing with the microbial transformation of an aporphine system.</description><subject>Aporphines - metabolism</subject><subject>Dealkylation</subject><subject>Fermentation</subject><subject>Microsporum - metabolism</subject><subject>Mitosporic Fungi - metabolism</subject><subject>Models, Biological</subject><subject>Mucor - metabolism</subject><subject>Mucorales - metabolism</subject><subject>Penicillium - metabolism</subject><subject>Streptomyces - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1975</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EglJYsUbKChaQ4kfsxktUKA8VgUR57KxJ4qhu7bjEqdT-PUFBwILVSHOP7mgOQkcEDwim5GLuMKYJBYzFFuoRTnGcpDjZRr12T2MqKNtD-yHMMcaMULaLdgnhUkjeQ9MHk9c-M2Aj5wttQ-TLyIFzYA1UkdMNZN6a4AbRY3ylwS42Fhrjqy-O4HNC4sK01MyvN7D09XJmKn2AdkqwQR9-zz56GV9PR7fx5PHmbnQ5iYHxpInLTCQi50TkWFOaEglpKbVIUpGBLjCnsigzVkgMkjJOOEtZUogs1SWIBGTB-uik613W_mOlQ6OcCbm2FirtV0GlVKZ8yFgLnnVg-2sItS7VsjYO6o0iWH05VH8ctvTxd-0qc7r4ZTtpbR53uQmNXv_EUC-UGLIhV9OnZ8WGb-_Pk_Grum_5046HPKi5X9VVK-Xfy5_3xYc6</recordid><startdate>19750801</startdate><enddate>19750801</enddate><creator>Rosazza, J. 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Chem</addtitle><date>1975-08-01</date><risdate>1975</risdate><volume>18</volume><issue>8</issue><spage>791</spage><epage>794</epage><pages>791-794</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>1159695</pmid><doi>10.1021/jm00242a006</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1975-08, Vol.18 (8), p.791-794 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Aporphines - metabolism Dealkylation Fermentation Microsporum - metabolism Mitosporic Fungi - metabolism Models, Biological Mucor - metabolism Mucorales - metabolism Penicillium - metabolism Streptomyces - metabolism |
| title | Microbial models of mammalian metabolism. O-Dealkylation of 10,11-dimethoxyaporphine |
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