Exercises
BIOCHEMISTRY
Unit 3 and 4
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What you need to know:
- The definition and classification of carbohydrates
- The importance of carbohydrates
- The structure of carbohydrates
- The difference between various isomers
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1. Sugar Alcohols
In the monosaccharide derivatives known as sugar alcohols, the carbonyl
oxygen is reduced to a hydroxyl group. For example, D-glyceraldehyde can
be reduced to glycerol. However, this sugar alcohol is no longer designated
D or L. Why?
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2. A Taste of Honey
The fructose in honey is mainly in the β-D-pyranose form. This is one of the
sweetest carbohydrates known, about twice as sweet as glucose; the β-D-
furanose form of fructose is much less sweet. The sweetness of honey
gradually decreases at a high temperature. Also, high fructose corn syrup (a
commercial product in which much of the glucose in corn syrup is
converted to fructose) is used for sweetening cold but not hot drinks. What
chemical property of fructose could account for both these observations?
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2. A Taste of Honey
High temperature
Low temperature
β-D-fructopyranose β-D-fructofuranose
3. Sugar Structures
Describe the common structural features and the differences for each pair:
(a) D-glucose and D-fructose
(b) Lactose and sucrose
(c) Cellulose and glycogen
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3. Sugar Structures
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3. Sugar Structures
Glycogen
Cellulose
4. Reducing Disaccharide
A disaccharide, which you know to be either maltose or sucrose, is treated
with Fehling’s solution, and red color is formed. Which sugar is it, and how do
you know?
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4. Reducing Disaccharide
Fehling test
saccharose
maltose
Boiling water bath
Bếp chưng cất thủy
for 2-3 minutes
Fehling’s reagent Cool the solution
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5. Structure of Cellulose
Explain in molecular terms why humans cannot use cellulose as a nutrient, but
goats and cattle can.
Glycogen / Amylopectin Cellulose
break
break Cellulase
Amylase 11
6. Physical Properties of Cellulose and Glycogen
The almost pure cellulose obtained from the seed threads of Gossypium
(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. Despite their markedly different physical properties, both
substances are (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.
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6. Physical Properties of Cellulose and Glycogen
Cellulose, a fibrous, tough, water-insoluble substance, is found in the
cell walls of plants.
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6. Physical Properties of Cellulose and Glycogen
Glycogen is the main storage polysaccharide of animal cells
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7. Structure of Starch
Add 1 – 2 drops of iodine solution (KI+I2) into a tube containing 5 ml of starch.
The solution in the tube quickly appears as a dark-blue color. However, this
color will disappear when the tube is heated. Explain this phenomenon. Will
the color reappear when cooling down? Why?
7. Structure of Starch
Iodine
Starch solution
Cooling
7. Structure of Starch
Amylose
Starch-iodine complex
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What you need to know:
- The definition of lipids
- The classification of lipids
- The structure and importance of lipids
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1. Omega-3 and omega-6 fatty acid Write the key convention and classify the
following fatty acids as omega-3, omega-6, or neither:
(a) Linolenic acid
(b) Linoleic acid
(c) Arachidonic acid
(d) Oleic acid
(e) cis-8,11,14-eicosatrienoic acid
(f) Eicosapentaenoic acid
(g) Docosahexaenoic acid
(h) Stearic acid
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From the methyl end:
Double bond between C-3 and C-4 are called omega-3 (ω-3) fatty acids
Double bond between C-6 and C-7 are omega-6 (ω-6) fatty acids
Stearic acid Oleic acid
Linoleic acid Linolenic acid
cis-8,11,14-eicosatrienoic acid Eicosapentaenoic acid
Arachidonic acid Docosahexaenoic acid (DHA) 20
2. Catalytic Hydrogenation of Vegetable Oils Catalytic hydrogenation, used in
the food industry, converts double bonds in the fatty acids of the oil
triacylglycerols to –CH2–CH2–. How does this affect the physical properties of
the oils?
–CH2=CH2– + H2 –CH2–CH2–
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2. Catalytic Hydrogenation of Vegetable Oils
Melting point ?
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3. Alkali Lability of Triacylglycerols A common procedure for cleaning the
grease trap in clothes or dishes is to add a product that contains sodium
hydroxide. Explain why this works.
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3. Alkali Lability of Triacylglycerols
Fatty acids are amphipathic compounds
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3. Alkali Lability of Triacylglycerols
Micelles
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4. Application of Wax In the produce department of supermarkets, vegetables
and fruits (oranges are an example) have been coated with wax for shipping
and storage. Suggest a reason why this is done.
Food waxing process 26
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4. Application of Wax
Paraffin wax
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Wax
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5. Membranes of Bacteria Suggest a reason why the cell membranes of
bacteria grown at 20°C tend to have a higher proportion of unsaturated fatty
acids than the membranes of bacteria of the same species grown at 37°C. In
other words, the bacteria grown at 37°C have a higher proportion of saturated
fatty acids in their cell membranes.
For more details:
María C. Mansilla et. al. (2004) Control of
Membrane Lipid Fluidity by Molecular
Thermosensors, JOURNAL OF BACTERIOLOGY,
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Oct. 2004, p. 6681–6688
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6. Preparation of Béarnaise Sauce During the preparation of béarnaise sauce,
egg yolks are incorporated into melted butter to stabilize the sauce and avoid
separation. The stabilizing agent in the egg yolks is lecithin
(phosphatidylcholine). Suggest why this works.
Béarnaise sauce components
White wine vinegar
Water
Melted butter
Egg yolk
Shallot
Tarragon
Lemon
Salt
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Pepper
6. Preparation of Béarnaise Sauce
Béarnaise sauce
components Lecithin (phosphatidylcholine)
White wine vinegar
Water
Melted butter Hydrophobic part
Egg yolk
Shallot
Tarragon
Lemon Hydrophilic part
Salt
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Pepper 30
7. Ninhydrin to Detect Lipids on TLC Plates Ninhydrin reacts specifically with
primary amines to form a purplish-blue product. A thin-layer chromatogram of
rat liver phospholipids is sprayed with ninhydrin, and the color is allowed to
develop. Which phospholipids can be detected in this way?
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7. Ninhydrin to Detect Lipids on TLC Plates
Glycerophospholipids
7. Ninhydrin to Detect Lipids on TLC Plates
Sphingolipids
8. Oil covering bird When water birds have had their feathers fouled with
crude oil after an oil spill, they are cleaned by rescuers to remove the spilled
oil. Why are they not released immediately after they are cleaned?
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8. Oil covering bird
Bird feathers are naturally wateproof by the preen oil
Bird preen oil example
2,4,6-Trimethylnonane 2-Hexadecanone
2,4,6,8,10-Pentamethyltridecane 4-Methyl Pentadecane
Elaina M. Tuttle et. al. (2014) Variation in Preen Oil Composition Pertaining to Season, Sex, and Genotype in
the Polymorphic White-Throated Sparrow, J Chem Ecol, 40:1025–1038 35
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