3D Structure
Biol. Function
References and links

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Synthesis The first total chemical synthesis of adrenaline was performed in 1904 by F. Stolz et al. pyrochatechol and chloro-acetylchloride react in the presence of phosphorchloridoxide to 3,4-dihydroxy- -chloracetophenone (Fries-rearrangement). After the conversion with methylamine, adrenalone will be reduced with sodiumamalgam to adrenaline.
Severall other syntheses also use adrenalone as starting material.
Biosynthesis 1: Phenylalanine-hydroxylase, 2: Tyrosine-hydroxylase, 3: Aromatic amino-acid decarboxylase, 4: Dopamine-beta-hydroxylase, 5: Phenylethanolamine- N-methyl- transferase
Five enzymes are involved in the pathway of the biosynthesis of adrenaline. The first enzyme is the iron containing phenylalanine-hydroxylase (also called phenylalanine-4-monooxygenase). The second enzyme, tyrosine-hydroxylase, contains iron, too, and catalyses the conversion of tyrosine to L-beta-(3,4-dihydroxyphenyl)- alpha-alanine (dopa). After decarboxylation of dopa to dopamine (aromatic amino-acid decarboxylase) the copper-containing enzyme dopamine-beta -hydroxylase converts dopamine to noradrenaline. The final enzyme noradrenaline-N-methyltransferase then methylates noradrenaline to adrenaline. The biosynthesis occurs in the adrenal medulla (see biologic function).
Last change: 1999-04-12