The amino acid tryptophan can be metabolized by a variety of organisms into a wealth of bioactive substances. Perhaps the best-known bioactive substance derived from tryptophan by the human body is serotonin.
A mammalian species uses the following metabolic pathway to obtain another bioactive substance. Draw the skeletal structure of the product of each metabolic process. (Show your product in the unionized state and omit any stereochemistry. You may copy the product out of one MarvinSketch window and use it in the next step as a template.)
(a) An enzyme of the hydroxylase family hydroxylates tryptophan at the 5-position.
(b) The resulting intermediate is then decarboxylated by an enzyme of the decarboxylase family.
(c) Next, aralkylamine N-acetyltransferase acetylates the primary amine.
(d) Finally, an enzyme of the O-methyltransferase family is used to methylate the phenolic oxygen of the last intermediate.