Microbial models of mammalian metabolism: O-dealkylation of para-alkoxybiphenyls. 1982

R V Smith, and S A Milton, and P J Davis

The potential of selected microorganisms to O-dealkylate alkyl aryl ethers in a manner analogous to mammalian systems has been studied. A total of 45 fungi and actinomycetes were screened for their ability to O-demethylate 4-methoxybiphenyl. Of the 20 organisms found to actively metabolize this substrate, 5 were chosen for additional study. Incubation with a series of five homologous 4-alkoxybiphenyls, 4-methoxy-, 4-ethoxy, 4-(1-propoxy)-, 4-(2-propoxy)-, and 4-(1-butoxy)biphenyl, revealed that all were O-dealkylated by Aspergillus flavus ATCC 24741. With Triton X-100 as a solubilizing agent, the relative rates and extent of O-dealkylation of the 4-alkoxybiphenyls, were studied with A. flavus. The methoxy and ethoxy dervatives were dealkylated in more than 90% yield after 72 h of incubation, while the higher homologs were cleaved to the extent of only about 10%. An analogous pattern of O-dealkylation has been reported in mammalian systems.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D003640 Dealkylation The removing of alkyl groups from a compound. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Dealkylations
D005658 Fungi A kingdom of eukaryotic, heterotrophic organisms that live parasitically as saprobes, including MUSHROOMS; YEASTS; smuts, molds, etc. They reproduce either sexually or asexually, and have life cycles that range from simple to complex. Filamentous fungi, commonly known as molds, refer to those that grow as multicellular colonies. Fungi, Filamentous,Molds,Filamentous Fungi,Filamentous Fungus,Fungus,Fungus, Filamentous,Mold
D001231 Aspergillus flavus A species of imperfect fungi which grows on peanuts and other plants and produces the carcinogenic substance aflatoxin. It is also used in the production of the antibiotic flavicin. Aspergillus parvisclerotigenus,Petromyces flavus
D001713 Biphenyl Compounds Whitish aromatic crystalline organic compounds made up of two conjoined BENZENE rings. Compounds, Biphenyl
D013302 Streptomyces A genus of bacteria that form a nonfragmented aerial mycelium. Many species have been identified with some being pathogenic. This genus is responsible for producing a majority of the ANTI-BACTERIAL AGENTS of practical value.

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