7168-66-3Relevant academic research and scientific papers
Demethylation of Reticuline and Derivatives Thereof with Fungal Cytochrome P450
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Paragraph 0561; 0562; 0566, (2021/07/31)
The invention relates to recombinant host cells that expresses one or more genes encoding a cytochrome P450 enzyme capable of N-demethylating and/O-demethylating reticuline and/or derivatives thereof, and also methods of producing a N-demethylated and/or O-demethylated reticuline and/or derivatives thereof, comprising cultivating the recombinant host of the invention in a culture medium under conditions in which the one or more genes encoding the cytochrome P450 enzymes is/are expressed. The reticuline and derivatives thereof are useful for providing access to naturally unavailable and chemically difficult-to-produce starting materials for opioids.
Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine
Machara, Ale?,Endoma-Arias, Mary Ann A.,Císa?ova, Ivana,Cox, D. Phillip,Hudlicky, Tomá?
, p. 1803 - 1813 (2016/07/06)
Thebaine was converted into its iron tricarbonyl complex, which underwent successive N- and O-demethylation with BrCN and BBr3, respectively. Decomplexation of the iron tricarbonyl moiety was accomplished with ammonium cerium(IV) nitrate (CAN) and base-catalyzed hydrolysis furnished nororipavine. When excess CAN was used the methoxydiene unit was converted into its C-14 nitrate that on hydrogenation and further hydrolysis furnished noroxymorphone. Full experimental and spectral data are provided for all key compounds.
Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions
Chaudhary, Vigi,Leisch, Hannes,Moudra, Alena,Allen, Blake,De Luca, Vincenzo,Cox, D. Phillip,Hudlicky, Tomas
experimental part, p. 1179 - 1193 (2010/04/26)
Morphine alkaloids and some of its derivatives (morphine, codeine, thebaine, oripavine, hydrocodone, and oxycodone) were subjected to fermentations with six fungal strains. The alkaloids were transformed to a variety of products via biological oxidations, reductions, and oxidative demethylations. The strain Cunninghamella echinulata proved to be the most effective for demethylations of all of the above compounds, except for morphine. The time profile of the conversion of 3-[14CH3]thebaine to 3-[ 14CH3]northebaine by C. echinulata cultures was also determined.
