Option A: Adrenaline (epinephrine)

Fig. 1. A chemical structure of adrenaline.

(a) With an asterisk, indicate the position of the chiral carbon(s) on the diagram above and state
the configuration. [2]
(b) State and explain which hydroxyl group is least acidic. [3]

(c) The body synthesizes adrenaline in a pathway starting with the phenylalanine, shown below
with the pKa values corresponding to its carboxyl and amino groups.

Fig. 2. A chemical structure of phenylalanine with pKa values.

i.

The pKa of 3-phenylpropanoic acid is 4.66. Explain why the carboxyl group on
phenylalanine has a lower pKa. [2]

ii.

Determine the isoelectric point of phenylalanine. [1]

(d) The first step in the biosynthesis of epinephrine involves the conversion of phenylalanine to
L-DOPA, the structure of which is shown below.

Fig. 3. A chemical structure of L-DOPA.

In the body, this is done by means of the enzymes phenylalanine hydroxylase and tyrosine
hydroxylase. Deduce a synthetic method for converting phenylalanine to L-DOPA. [5]