CHEM43

PROBLEM SET ON CARBOHYDRATES AND LIPIDS

1. Why would a bilayer containing only gangliosides be unstable?

2. Lactose exists in two anomeric forms but, as of date, anomeric forms of

sucrose are non-existent. Explain.

3. A polysaccharide of unknown structure was isolated, subjected to exhaustive

methylation, and hydrolyzed. Analysis of the products revealed three
methylated sugars in the ratio 20:1:1. The sugars were 2,3,4-tri-O-methylated-
D-glucose, 2.4-di-O-methyl-D-glucose, and 2,3,4,6-tetra-O-methyl-D-glucose.
What is the structure of the polysaccharide?

4. During gel electrophoresis, glycoproteins migrate as relatively diffuse bands

whereas non-glycosylated proteins typically migrate as narrow, well-defined
bands. Explain the difference in electrophoretic behavior.

5. Draw all the possible triacylglycerols that can be constructed from glycerol,
palmitic acid, and oleic acid. Rank them in order of increasing melting point.

6. Which of the following pairs of sugars are epimers of each other?

A. D-fructose and L-fructose
B. D-arabinose and D-ribose
C. D-ribose and D-ribulose
D. D-sorbose and D-psicose

7. Name the following lipid:

8. The almost pure cellulose obtained from the seed threads of cotton is tough,
fibrous, and completely insoluble in water. In contrast, glycogen obtained from
muscle or liver disperses readily in hot water to make a turbid solution.
Although they have markedly different physical properties, both substances
are composed of (1→4)-linked-D-glucose polymers of comparable molecular
weight. What structural features of these two polysaccharides underlie their
different physical properties? Explain the biological advantages of their
respective properties.

9. Name the products of mild hydrolysis with dilute NaOH of 1-stearoyl-2,3-

dipalmitoyl-glycerol.
10. Indicate whether the following compounds are likely to cross a membrane by
nonmediated or mediated transport:
A. Ethanol
B. Glycine
C. Cholesterol
D. ATP

11. The inner leaflet (monolayer) of the human erythrocyte membrane consists of
predominantly of phosphatidylethanolamine and phosphatidylserine. The
outer leaflet consists predominantly of phosphatidylcholine and
sphingomyelin. Although the phospholipid components of the membrane can
diffuse the fluid bilayer, this sidedness is preserved at all times. How?

12. Endothelial cells and pericytes in the retina of the eye have different
mechanisms for glucose uptake. The figure shows the rate of glucose uptake
for each type of cell in the presence of increasing amounts of sodium. What
do these results reveal about the glucose transporter in each cell type?