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CHEM151 Name (Print) /ID #: ________________________________________

Biochemistry 1
Spring 2015 (50 points)
Quiz #1
1. 2.
3. 1.
1. Fill in the following table: (12 points)

2. A pharmaceutical molecule with antifungal properties is only active when in the protonated state
(HA). The deprotonated state and negatively charged (A-) is inactive. If the pKa of this drug is 10.0:
(12 points)

a. Calculate the ratio of protonated to deprotonated compound at physiological pH (7.4).

b. Is this drug likely to be a useful pharmaceutical agent?

Answer:

a. Calculate the ratio of protonated to deprotonated compound at physiological pH (7.4).


(8 points)

Since we are given both the pH and pK of the compound, we can use the Henderson
Hasselbalch equation to solve for the ratio of [HA] to [A-].

pH = pKa - log([HA] / [A-])


log([HA] / [A-]) = pKa pH
log([HA] / [A-]) = 10.0 7.4
log([HA] / [A-]) = 2.6
([HA] / [A-]) = 398.11
([HA] / [A-]) = 400

The ratio of protonated (inactive) compound to deprotonated (active) compound is 400 to 1 at


physiological pH.

b. Is this drug likely to be a useful pharmaceutical agent? (2 points)

Since the vast majority of the compound is in the active form at physiological pH, it is likely
to be a useful pharmaceutical agent.

3. I have the peptide with the sequence TEST. Write the structure of this peptide at pH 2 with all charged
groups in their proper ionization state.(10 points) (1 per AA; 2 for amino terminal (amino group and
charge); 2 points for carboxyl; 2 for peptide bond formation)

4. The skeletal structures of the two amino acids, glycine and glutamic acid, are given below
along with the values of the relevant acid dissociation constants (pKa). (16 points)

a. For an aqueous solution of glycine (Gly) alone, calculate the value of pH at which the ratio of
the concentration of neutral glycine zwitterion to the concentration of deprotonated anion is
10-4 (6 points)
b. Draw the skeletal structure of glutamic acid (Glu) when it is solvated in an aqueous solution under
each of the following conditions (9 points each)

i. pH = 1.5 pH = 14 pH = pI

ii. Calculate the value of pH at which glutamic acid (Glu) exists as the neutral
zwitterion. (1 point)