CHEM1280 Problem Set 10

(For practice only. Don't submit your answers)

1. Draw the form of aspartate that predominates at the following pH. (The pKa values of
aspartate can be found in the lecture notes.)
a. pH = 1.0 b. pH = 2.6 c. pH = 6.0 d. pH = 11.0

2. When an α-amino acid is treated with DCC, a 2.5-diketopiperazine results as shown

below. Propose a mechanism for the following reaction using the curved arrows to show
the flow of electrons.

3. In acidic solutions, nucleosides are hydrolyzed to a sugar and a heterocyclic base.

Propose a mechanism for the following reaction using the curved arrows to show the flow
of electrons.

4. In the following reaction, glutamate is converted into glutamine. Draw the principle form
of glutamate present at its isoelectric point. Propose a mechanism for this reaction using
the curved arrows to indicate the flow of electrons.