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SUMMARY EXAM #2 December 3, 2003
150 Total Points
NAME__________KEY_________________ UTEID________________
Fill in your answers to the questions below ON THIS SHEET. Keep your
answers brief. ONLY ANSWERS WITHIN THE BOXED AREAS WILL BE
GRADED.
HPLC Lab Questions (Dr. Kerwin)
B. Draw on the TLC plate three spots of the following approximate Rf values
(you can estimate the position on the plate – you do not need a ruler):
• Rf = 0.9
• Rf = 0.5
• Rf = 0.1
CO2H
CO2H O
solvent front
Rf = 0.9, Z
Rf = 0.5, Y
Rf = 0.1, X
origin
3. (7 points) You have completed the HPLC lab by determining the reverse-phase
HPLC retention time for a series of barbiturates using an aqueous mobile phase, pH 7.4.
You have plotted these retention times versus the apparent partition coefficients (logPapp)
for these drugs (see the plot below).
Use the graph below to answer the following question: A barbiturate with a pKa of 7.4
gives a retention time of 7.0 minutes. What is the intrinsic partition coefficient (Log Po)
for this barbiturate?
2.8
2.6
2.4
y = 0.1645x + 0.2483
2.2
R2 = 0.9964
2
1.8
LogPapp
1.6
1.4
1.2
0.8
0.6
0.4
0.2
0
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
LogPo = 1.7
Visualization Lab Questions (Dr. Dalby)
CH2
CH2
H CH2
N
O CH2
C CH NH
HN
H2C C O
CH OH
CH CH
C CH3
O
NH
HN H
N CH C
CH C
O
CH3
CH2 O
H2C
HO O
= Nitrogen
= Oxygen
Asn
6. (8 points) What amino acid is this?
Pro
7. (16 points) What amino acids are present in the structure below? Is it a typical
peptide? Explain your answer.
Attached you will find the composite metabolic tree that was developed in the liver game.
The following three questions relate to that scheme.
Circle the letter corresponding to the single best answer on this exam paper – do not
use the Scantron.
23. (7 points) On the upper right part of the diagram, we see a product resulting from
omega-hydroxylation and then an acid product generated from that alcohol. Why is there
no aldehyde ‘intermediate’ structure shown where the question mark (“?”) is?
A. You cannot form an aldehyde from a primary alcohol.
B. The production of an acid from a primary alcohol does not go through an
aldehyde intermediate.
C. While the production of an acid from a primary alcohol usually goes through an
aldehyde intermediate, there are other metabolic pathways that do not require this
(i.e., oxidation of the alcohol in one step to the acid). That’s what we’re seeing
here.
D. There was probably aldehyde formed, but apparently it went to the sulfate
conjugate (in levels of <1% so it’s not shown).
E. None of the above.
25. (7 points) At the bottom of the page we see O-dealkylation to form a phenol, and
from that phenol, both sulfate and glucuronide conjugates are generated. Why are both
generated?
A. The students who were passed the ‘phenol’ must have been assigned phase-2
reactions. For any one of those students, that student would have had the option
of carrying out sulfate conjugation or glucuronide formation (their choice), and so
a mixture resulted.
B. Some students who were passed the ‘phenol’ must have been assigned glutathione
transferase, and some students were assigned UDP-glucuronyl transferase.
C. Some students who were passed the ‘phenol’ must have been assigned UDP-
glucuronyl transferase, and some students were assigned aryl sulfotransferase.
D. Some students who were passed the ‘phenol’ must have been assigned aryl
sulfotransferase, and some students were assigned glutathione transferase.
E. None of the above.
26. (7 points) At the beginning of the lab session, you and your lab partner were given
the molecule shown below and asked to complete as much of a metabolic tree as you
could. After the Flash® tutorials, you were asked to return to the scheme you started and
add any additional routes of metabolism that you could. In this second step, how many
additional metabolites did you and your partner add to this scheme (Note: yes, this is
really a test question. Be honest; do not inflate this number).
27. (7 points) On the tutorial for acetaminophen (structure shown below) a number of
phase-2 metabolites were generated in the metabolic scheme. For the statements that
follow, when is the first time an incorrect statement is made?