3423-27-6Relevant articles and documents
Solid-phase synthesis of tertiary N-Methyl amines including tropanes
Sienkiewicz, Michal,Lazny, Ryszard
scheme or table, p. 5 - 8 (2010/10/04)
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Further investigation of the N-demethylation of tertiary amine alkaloids using the non-classical Polonovski reaction
Thavaneswaran, Shanti,Scammells, Peter J.
, p. 2868 - 2871 (2007/10/03)
The iron salt-mediated Polonovski reaction efficiently N-demethylates certain opiate alkaloids. In this process, the use of the hydrochloride salt of the tertiary N-methyl amine oxide was reported to give better yields of the desired N-demethylated product. Herein, we report further investigation into the use of N-oxide salts in the iron salt-mediated Polonovski reaction. An efficient approach for the removal of iron salts that greatly facilitates isolation and purification of the N-nor product is also described.
Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura
Boswell, Henry D.,Draì?ger, Birgit,McLauchlan, W. Russell,Portsteffen, Andreas,Robins, David J.,Robins, Richard J.,Walton, Nicholas J.
, p. 871 - 878 (2007/10/03)
The enzymes N-methylputrescine oxidase (MPO), the tropine-forming tropinone reductase (TRI), the pseudotropine-forming tropinone reductase (TRII), the tropine:acyl-CoA transferase (TAT) and the pseudotropine:acyl-CoA transferase (PAT) extracted from transformed root cultures of Datura stramonium and a Brugmansia candida x aurea hybrid were tested for their ability to accept a range of alternative substrates. MPO activity was tested with N-alkylputrescines and N-alkylcadaverines as substrates. TRI and TRII reduction was tested against a series of N-alkylnortropinones, N- alkylnorpelletierines and structurally related ketones as substrates. TAT and PAT esterification tests used a series of N-substituted tropines, pseudotropines, pelletierinols and pseudopelletierinols as substrates to assess the formation of their respective acetyl and tigloyl esters. The results generally show that these enzymes will accept alien substrates to varying degrees. Such studies may shed some light on the overall topology of the active sites of the enzymes concerned.