BIOSC

1000

Sample Problem Answers Lecture 4

1. Identify the hydrogen bond donor and acceptor groups, excluding the alpha-amino and
alpha carboxylic acid groups, in

a. Aspartic acid - side chain carboxylic acid is both acceptor and donor
b. Serine - side chain hydroxyl donor
c. Glutamic acid - side chain carboxylic acid is both acceptor and donor


2. Tyrosine has a very low water solubility. If you were to compare solutions made with X
number of individual tyrosine molecules with a solution containing tyrosine peptides
containing an equivalent number of tyrosine molecules, which would be more soluble?
Why?

The individual amino acids, because they have free amino and carboxyl groups to
contribute to hydrogen bonding with the water. The peptides have only a single
amino terminal and carboxy terminal for multiple tyrosine residues.


3. The artificial sweetener NutraSweet, also called aspartame, is a simple dipeptide,
aspartylphenylalanine methyl ester (the free carboxyl of the dipeptide is esterified to
methyl alcohol). Draw the structure of aspartame, showing the ionizable groups in the
form they have at pH 7.










Note that when you draw structures of amino acids/peptides for the quiz and exams I
would like you to draw all of the atoms (like above) and not use the organic shorthand
(except for aromatic rings that dont contain N, like above). This way I can be certain
you know what atoms those structures represent.

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BIOSC 1000

4. In what order will the following amino acids be eluted from a column of P-cellulose
(phosphate groups linked to cellulose) by a buffer at pH 6: arginine, aspartic acid,
histidine, and leucine?

P-cellulose is a strongly acidic (negatively charged), so positively charged molecules
will adhere most tightly. Thus, the amino acids should elute in the following order:
aspartic acid (negatively charged at pH 6), leucine (neutral), histidine (weakly
positive at pH 6), arginine (strongly positive at pH 6).


5. In what order will the following proteins be eluted from a size-exclusion column?


Protein
Molecular
Size-exclusion separates proteins according to mass,
Mass
with larger proteins moving more quickly through
(kD)
the column while small proteins are retarded
Catalase
222
because they enter the support matrix.
- chymotrypsin 21.6

Concanavalin B 42.5
The first protein eluted will be catalase, followed in
Lipase
6.7
order by concanavalin B, - chymotrypsin,
myoglobin
16.9
myoglobin, and lipase.



6. The neurotransmitter GABA (-aminobutryic acid) is thought to bind to specific
receptor proteins in nerve tissue. Design a procedure for the partial purification of such
a receptor protein.


This is the ideal opportunity to use affinity chromatography. GABA can be
chemically attached to an inert resin and a homogenate of brain tissue poured over
the column. The receptor should selectively bind to the column and it can be eluted
with excess GABA

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