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The biosynthesis of the tropane alkaloids have attracted intense interest because of their high physiological activity as well as the presence of the bicyclic tropane core. [12] Final stages in the pathway for the biosynthesis of the tropane alkaloid cocaine.
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. [2] [3] Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone. [4]
The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N ...
Hyoscyamine (also known as daturine or duboisine) is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna (deadly nightshade).
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine , among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca ) and Solanaceae (including mandrake , henbane , deadly nightshade , datura , potato , tomato ).
The biosynthesis of the tropane alkaloid is still not understood. Hemscheidt proposes that Robinson's acetonedicarboxylate emerges as a potential intermediate for this reaction. [149] Condensation of N-methylpyrrolinium and acetonedicarboxylate would generate the oxobutyrate. Decarboxylation leads to tropane alkaloid formation.
Tropane alkaloid biosynthesis is another avenue of defense with codons positively selected and expanded in the Datura branch. It is aided by the tropane alkaloid Littorine rearrangement which is very important to scopolamine and atropine/hyoscyamine production, all of which serve to debilitate any organism that would come into contact with them.
Tropane derivatives [57] ... In the biosynthesis of alkaloids, such reactions may take place within a molecule, [188] such as in the synthesis of piperidine: [41]