CHM3270: Homework #2

Due: Mon 2/10/2020

1. Two amino acids are either not a standard -amino acid or in the S configuration. Which
residues are they, and how are they different? Illustrate your reasoning with chemical
structures.

2. For the amino acid arginine, draw the Fischer projection and label the functional groups. What
are the ionization states at pH 2.6, 8.0, and 11.2, and what are the overall charges of arginine at
these pH values?

3. Estimate the isoelectric point of a Ser-His dipeptide. Explain why this value is only an estimate.

4. The two CH atoms of Gly are said to be prochiral because when one of them is replaced by
another group, C becomes chiral. Draw a Fischer projection of Gly and indicate which H must
be replaced with CH3 to yield D-Ala.

5. Draw the pentapeptides QPACI and DCVKF and answer these questions.

a. One of these two pentapeptides may have a cis peptide. Which one?
b. Re-draw the pentapeptide with your cis-peptide.
c. Explain your rationale for why this pentapeptide may have a cis-peptide. Why does the
trans conformation predominate?

6. Why is the order of amino acids in a peptide more important than the identity of the amino
acids in a peptide? (Describe what may happen if the order of amino acids were scrambled.)

Other practice problems (you do not need to turn these in but are recommended for practice):

Ch.4, odd questions

Remember to practice drawing and naming the 20 standard amino acids!