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Chapter 7 Carbohydrates and Glycobiology
Multiple Choice Questions

1. Monosaccharides and disaccharides
Page: 243 Difficulty: 1 Ans: C
To possess optical activity, a compound must be:
A) a carbohydrate.
B) a hexose.
C) asymmetric.
D) colored.
E) D-glucose.

Page: 244 Difficulty: 2 Ans: B
Which of the following monosaccharides is not an aldose?
A) Erythrose
B) Fructose
C) Glucose
D) Glyceraldehyde
E) Ribose

Pages: 244–245 Difficulty: 2 Ans: C
The reference compound for naming D and L isomers of sugars is:
A) fructose.
B) glucose.
C) glyceraldehyde.
D) ribose.
E) sucrose.

Page: 245 Difficulty: 2 Ans: D
When two carbohydrates are epimers:
A) one is a pyranose, the other a furanose.

B) one is an aldose, the other a ketose.
C) they differ in length by one carbon.
D) they differ only in the configuration around one carbon atom.
E) they rotate plane-polarized light in the same direction.
Chapter 7 Carbohydrates and Glycobiology 81

Pages: 245–246 Difficulty: 2 Ans: B
Which of the following is an epimeric pair?
A) D-glucose and D-glucosamine

B) D-glucose and D-mannose
C) D-glucose and L-glucose
D) D-lactose and D-sucrose
E) L-mannose and L-fructose

Pages: 246–247 Difficulty: 2 Ans: D
Which of following is an anomeric pair?
A) D-glucose and D-fructose

B) D-glucose and L-fructose
C) D-glucose and L-glucose
D) -D-glucose and -D-glucose
E) -D-glucose and -L-glucose

When the linear form of glucose cyclizes, the product is a(n):
A) anhydride.
B) glycoside.
C) hemiacetal.
D) lactone.
E) oligosaccharide.

Page: 248 Difficulty: 2 Ans: E
Which of the following pairs is interconverted in the process of mutarotation?
A) D-glucose and D-fructose

B) D-glucose and D-galactose
C) D-glucose and D-glucosamine
D) D-glucose and L-glucose
E) -D-glucose and -D-glucose

Pages: 250–253 Difficulty: 2 Ans: E
Which of the following is not a reducing sugar?
A) Fructose
B) Glucose
C) Glyceraldehyde
D) Ribose
E) Sucrose
82 Chapter 7 Carbohydrates and Glycobiology

Which of the following monosaccharides is not a carboxylic acid?
A) 6-Phospho-gluconate
B) Gluconate
C) Glucose
D) Glucuronate
E) Muramic acid

D-Glucose is called a reducing sugar because it undergoes an oxidation-reduction reaction at the
anomeric carbon. One of the products of this reaction is:
A) D-galactose.
B) D-gluconate.
C) D-glucuronate.
D) D-ribose.
E) muramic acid.

Hemoglobin glycation is a process where is attached to hemoglobin.
A) glycerol; covalently
B) glucose; enzymatically
C) glucose; non-enzymatically
D) N-acetyl-galactosamine; enzymatically
E) galactose; non-enzymatically

When forming the disaccharide maltose from two glucose monosaccharides:
A) water is eliminated.
B) a hemiacetal is converted to an acetal.
C) the resulting dissacharide is no longer a reducing sugar.
D) Both A and B
E) A, B, and C above

Page: 252 Difficulty: 2 Ans: A
From the abbreviated name of the compound Gal(1 → 4)Glc, we know that:
A) C-4 of glucose is joined to C-1 of galactose by a glycosidic bond.

B) the compound is a D-enantiomer.
C) the galactose residue is at the reducing end.
D) the glucose is in its pyranose form.
E) the glucose residue is the  anomer.
15. Polysaccharides
Pages: 255 Difficulty: 1 Ans: D
Starch and glycogen are both polymers of:
A) fructose.
B) glucose1-phosphate.
C) sucrose.
D) -D-glucose.
E) -D-glucose.
16. Polysaccharides
Which of the following statements about starch and glycogen is false?
A) Amylose is unbranched; amylopectin and glycogen contain many (1 → 6) branches.

B) Both are homopolymers of glucose.
C) Both serve primarily as structural elements in cell walls.
D) Both starch and glycogen are stored intracellularly as insoluble granules.
E) Glycogen is more extensively branched than starch.
17. Polysaccharides
Which of the following statements about hydrogen bonding in glycogen and cellulose is true?
A) Glycogen forms more internal H-bonds than cellulose.

B) Extensive internal hydrogen bonding makes cellulose more water soluble than glycogen.
C) Extensive hydrogen bonding with water makes cellulose more soluble than glycogen.
D) Glycogen primarily forms hydrogen bonds within a single chain.
E) The hydrogen bonding in cellulose favors a helical conformation.
18. Polysaccharides
Following complete hydrolysis of a sample of glycogen and a sample of cellulose, which of the
following must be true?
A) The glycogen sample is more soluble than the cellulose sample.

B) The cellulose sample is more soluble than the glycogen sample.
C) Both samples consist of a mixture of -D-glucose and -D-glucose.
D) The glycogen sample has a higher ratio of -D-glucose than the cellulose sample.
E) The cellulose sample contains only -D-glucose.
19. Polysaccharides
Which of the following is a heteropolysaccharide?
A) Cellulose
B) Chitin
C) Glycogen
D) Hyaluronate
E) Starch
20. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

The basic structure of a proteoglycan consists of a core protein and a:
A) glycolipid.
B) glycosaminoglycan.
C) lectin.
D) lipopolysaccharide.
E) peptidoglycan.

Which of the following statements about heparan sulfate is not true?
A) Sulfation of heparan sulfate to form NS domains is important for its role as an anti-coagulant.
B) Heparan sulfate can promote protein-protein interactions via the NS domains.
C) The secondary structure of heparan sulfate is completely random.
D) The NA domains of heparan sulfate contain no sulfation.
E) The core repeating structure of heparan sulfate is made up of alternating GlcNAc and GlcA.

Pagse: 266–267 Difficulty: 2 Ans: A
In glycoproteins, the carbohydrate moiety is always attached through the amino acid residues:
A) asparagine, serine, or threonine.

B) aspartate or glutamate.
C) glutamine or arginine.
D) glycine, alanine, or aspartate.
E) tryptophan, aspartate, or cysteine.

Which of the following is a dominant feature of the outer membrane of the cell wall of gram negative
bacteria?
A) Amylose
B) Cellulose
C) Glycoproteins
D) Lipopolysaccharides
E) Lipoproteins
24. Carbohydrates as informational molecules: the sugar code

The biochemical property of lectins that is the basis for most of their biological effects is their ability
to bind to:
A) amphipathic molecules.
B) hydrophobic molecules.
C) specific lipids.
D) specific oligosaccharides.
E) specific peptides.

Which of the following statements concerning sialic acid residues on glycoproteins is true?
A) Sialic residues on erythrocytes are recognized by lectins, leading to removal of the erythrocytes.
B) Sialic residues on ceruloplasmin are recognized by lectins, leading to removal of ceruloplasmin.
C) Sialic residues are removed by neuraminidases.
D) The anti-viral drug oseltamavir accelerates the removal of sialic acid residues.
E) Both A and B above

Why is it surprising that the side chains of tryptophan residues in lectins can interact with sugars?
A) Because the side chain of tryptophan is hydrophilic and sugars are hydrophobic
B) Because the side chain of tryptophan is (–) charged and sugars are generally (+) charged or
neutral
C) Because the side chain of tryptophan can make hydrogen bonds and sugars cannot.
D) Because the side chain of tryptophan is hydrophobic and sugars are generally hydrophilic
E) None of the above
27. Working with carbohydrates

Which of the following is not a reason that it is difficult to study oligosaccharide composition from
biological systems?
A) Oligosaccharides are often branched.

B) Oligosaccharides often have a high negative charge density.
C) Oligosaccharides have a variety of linkages (e.g., 1→6 or 1→4).
D) Oligosaccharides have too much conformational flexibility.
E) There are no specific glycosidase enzymes that can be used to selectively digest oligosaccharides.

Pages: 274–275 Difficulty: 2 Ans: A
Which of the following techniques is not commonly used to study oligosaccharide structures?
A) X-ray crystallography
B) Matrix-assisted laser desorption/ionization mass spectroscopy (MALDI-MS)
C) Nuclear magnetic resonance (NMR)
D) Complete chemical synthesis
E) Oligosaccharide microarrays
Short Answer Questions

Pages: 244–246 Difficulty: 1
Explain why all mono- and disaccharides are soluble in water.
Ans: These compounds have many hydroxyl groups, each of which can hydrogen bond with water.
(See Chapter 4.)

This compound is L-glyceraldehyde. Draw a stereochemically correct representation of C-1 and C-2
of D-glucose.
CHO
|
HO—C—H
|
CH2OH
Ans: In D-glucose, the positions of the —H and —OH on C-2 are the reverse of those for C-2 of L-
glyceraldehyde. (Compare Fig. 7-1, p. 236, with Fig. 7-2, p. 236.)

Categorize each of the following as an aldose, a ketose, or neither.
H H H H H
H C OH O C H C OH HO C H C O
C O H C OH HO C H H C OH H C OH
H C OH HO C H HO C H C O H C H
H H H H H
(a) (b) (c) (d) (e)
Ans: Molecules (b) and (d) are aldoses; (a) is a ketose; (c) and (e) are neither.

Define each in 20 words or fewer:
(a) anomeric carbon
(b) enantiomers
(c) furanose
(d) pyranose
(e) glycoside
(f) epimers
(g) aldose
(h) ketose
Ans: (a) The anomeric carbon is the carbonyl carbon atom of a sugar, which is involved in ring
formation. Once the anomeric carbon is involved in a glycosidic bond it is the only carbon with more
than one oxygen. (b) Enantiomers are stereoisomers that are nonsuperimposable mirror images of
each other. (c) Furanose is a sugar with a five-membered ring. (d) Pyranose is a sugar with a six-
membered ring. (e) A glycoside is an acetal formed between a sugar anomeric carbon hemi-acetal
and an alcohol, which may be part of a second sugar. (f) Epimers are stereoisomers differing in
configuration at only one asymmetric carbon. (g) An aldose is a sugar with an aldehyde carbonyl
group. (h) A ketose is a sugar with a ketone carbonyl group.

(a) Draw the structures of both anomers of glucose in the pyranose ring form. (b) How many
asymmetric carbons (chiral centers) does each of these structures have? (c) How many stereoisomers
of the glucose are theoretically possible?
Ans: (a) See Fig. 7-7. (b) The number of chiral centers is 5; all the carbons except C-6. (c) The
number of possible stereoisomers for a compound with n chiral centers is 2n; in this case, 25, or 32
possible isomers.

Identify all the epimeric pairs in the structures shown below.
Ans: Epimeric pairs should have one carbon of altered stereochemistry compared to each other, as
long as that carbon is not the anomeric carbon. Remember that all of the pyranoses shown readily
interconvert to the linear version and to their opposite anomer. Therefore, C and D are anomers of
each other, but are both epimers of A. Likewise, E and F are anomers of each other, but both are
epimers of B.

In the following structure:
(a) How many of the monosaccharide units are furanoses and how may are pyranoses? (b) What is
the linkage between the two monosaccharide units? (c) Is this a reducing sugar?
Explain.
Ans: (a) 2 pyranoses; (b) 1 → 4; (c) yes. There is a free anomeric carbon on one of the
monosaccharide units that can undergo oxidation upon ring-opening.

Pages: 251 Difficulty: 2
In measuring long-term glucose levels in the bloodstream, glycated hemoglobin must be separated
from unmodified hemoglobin to determine the percentage of glycated hemoglobin. Suggest a simple
chromatographic method by which this separation can be performed.
Ans: Free hemoglobin has more positively charged residues (both lysine side chains and free amino
ends) than glycated hemoglobin, where these amines have been converted to uncharged Schiff bases
(see Box 7-1). Therefore, free hemoglobin is more positively charged than glycated hemoglobin and
ion exchange chromatography could be used. (Whether one uses anion or cation exchange
chromatography depends on the pI of hemoglobin (6.9) and the pH of the buffer; see Chapter 3.)

(a) Define “reducing sugar.” (b) Show the reaction product of glucose after it is used as a reducing
sugar. (c) Explain why fructose is also considered a reducing sugar. (Hint: It must first undergo a
chemical conversion.) (d) Sucrose is a disaccharide composed of glucose and fructose
(Glc(1 → 2)Fru). Explain why sucrose is not a reducing sugar, even though both glucose and
fructose are.
Ans: (a) A reducing sugar is one with a free carbonyl carbon (aldehyde) that can be oxidized to the
carboxylic acid by Cu2+ or Fe3+. (b) You should have converted the aldehyde carbon of linear
glucose to a carboxylic acid. (c) Fructose is a ketose, which cannot be readily oxidized; that is, it
does not act as a reducing agent in its unaltered form. Fructose must first undergo an isomerization to
glucose, a reaction that is readily catalyzed by acidic or basic conditions. (d) The carbonyl carbons of
sucrose are C-1 of glucose and C-2 of fructose. When the carbonyl carbons are involved in
glycosidic linkages, they are no longer accessible to oxidizing agents. In sucrose (Glc(1 → 2)Fru),
both oxidizable carbons are involved in the glycosidic linkage.
38. Polysaccharides
Match these molecules with their biological roles.
(a) glycogen __ viscosity, lubrication of extracellular secretions
(b) starch __ carbohydrate storage in plants
(c) trehalose __ transport/storage in insects
(d) chitin __ exoskeleton of insects
(e) cellulose __ structural component of bacterial cell wall
(f) peptidoglycan __ structural component of plant cell walls
(g) hyaluronate __ extracellular matrix of animal tissues
(h) proteoglycan __ carbohydrate storage in animal liver
Ans: g; b; c; d; f; e; h; a
39. Polysaccharides
The number of structurally different polysaccharides that can be made with 20 different
monosaccharides is far greater than the number of different polypeptides that can be made with 20
different amino acids if both polymers contain an equal number (say 100) of total residues. Explain
why.
Ans: Because virtually all peptides are linear (i.e., are formed with peptide bonds between the -
carboxyl and -amino groups), the variability of peptides is limited by the number of different
subunits. Polysaccharides can be linear or branched, can be - or -linked, and can be joined 1 → 4,
1 → 3, 1 → 6, etc. The number of different ways to arrange 20 different sugars in a branched
oligosaccharide is therefore much larger than the number of different ways a peptide could be made
with an equal number of residues.
40. Polysaccharides
Describe one biological advantage of storing glucose units in branched polymers (glycogen,
amylopectin) rather than in linear polymers.
Ans: The enzymes that act on these polymers to mobilize glucose for metabolism act only on their
nonreducing ends. With extensive branching, there are more such ends for enzymatic attack than
would be present in the same quantity of glucose stored in a linear polymer. In effect, branched
polymers increase the substrate concentration for these enzymes.
41. Polysaccharides
Page: 256 Difficulty: 2
Explain how it is possible that a polysaccharide molecule, such as glycogen, may have only one
reducing end, and yet have many nonreducing ends.
Ans: The molecule is branched, with each branch ending in a nonreducing end. (See Fig. 7-13c.)
42. Polysaccharides
What is the biological advantage to an organism that stores its carbohydrate reserves as starch or
glycogen rather than as an equivalent amount of free glucose?
Ans: The polymers are essentially insoluble and contribute little to the osmolarity of the cell, thereby
avoiding the influx of water that would occur with the glucose in solution. They also make the uptake
of glucose energetically more feasible than it would be with free glucose in the cell.
43. Polysaccharides
Draw the structure of the repeating basic unit of (a) amylose and (b) cellulose.
Ans: (a) For the structure of amylose, see Fig. 7-13a. The repeating unit is -D-glucose linked to -D-
glucose; the glycosidic bond is therefore (1 → 4). (b) Cellulose has the same structure as amylose,
except that the repeating units are -D-glucose and the glycosidic bond is (1 → 4). (See Fig. 7-14.)
44. Polysaccharides
Explain in molecular terms why humans cannot use cellulose as a nutrient, but goats and cattle can.
Ans: The ruminant animals have in their rumens microorganisms that produce the enzyme cellulase,
which splits the (1 → 4) linkages in cellulose, releasing glucose. Humans do not produce an
enzyme with this activity; the human digestive enzyme -amylase can split only (1 → 4) linkages
(such as those in glycogen and starch).
45. Polysaccharides
The glycosaminoglycans are negatively charged at neutral pH. What components of these polymers
confer the negative charge?
–
Ans: Uronic acids such as glucuronic acid, and sulfated hydroxyl groups, such as GalNAc4SO3 and
–
GlcNAc6SO3 . (See Fig. 7-22.)

Sketch the principal components of a typical proteoglycan, showing their relationships and
connections to one another.
Ans: A typical proteoglycan consists of a core protein with covalently attached glycosaminoglycan
polysaccharides, such as chondroitin sulfate and keratin sulfate. The polysaccharides generally attach
to a serine residue in the protein via a trisaccharide (gal–gal–xyl). (See Fig. 7-24, p. 253.)

Describe the differences between a proteoglycan and a glycoprotein.
Ans: Both are made up of proteins and polysaccharides. In proteoglycans, the carbohydrate moiety
dominates, constituting 95% or more of the mass of the complex. In glycoproteins, the protein
constitutes a larger fraction, generally 50% or more of the total mass.

Describe the structure of a proteoglycan aggregate such as is found in the extracellular matrix.
Ans: A proteoglycan aggregate is a supramolecular assembly of proteoglycan monomers. Each

monomer consists of a core protein with multiple, covalently linked polysaccharide chains. Hundreds
of these monomers can bind noncovalently to a single extended molecule of hyaluronic acid to form
large structures.

How do oligosaccharide portions of glycoproteins change the properties of the proteins?
Ans: Hydrophilic carbohydrates can alter the polarity and solubility of the proteins. Steric and charge
interactions may influence the conformation of regions of the polypeptide and protect it from
proteolysis. Carbohydrates attached to proteins can provide binding sites for lectins.

Test Bank for Lehninger Principles of Biochemistry Sixth Edition

Describe the process by which “old” serum glycoproteins are removed from the mammalian
circulatory system.
Ans: Newly synthesized serum glycoproteins bear oligosaccharide chains that end in sialic acid.
With time, the sialic acid is removed. Glycoproteins that lack the terminal sialic acid are recognized
by asialoglycoprotein receptors in the liver, internalized, and destroyed.

What are lectins? What are some biological processes that involve lectins?
Ans: Lectins are proteins that bind to specific oligosaccharides. They interact with specific cell-
surface glycoproteins thus mediating cell-cell recognition and adhesion. Several microbial toxins and
viral capsid proteins, which interact with cell surface receptors, are lectins.

Briefly explain how the drugs Tamiflu and Relenza work to prevent the flu.
Ans: A newly formed flu virus needs to get out of its host cell in order to infect new cells and make
more virus. As the new virus buds off the host cell, it initially binds (via lectins) to cell surface
receptors located in the membrane that are specific for sialic acid residues. The release from these
receptors is facilitated by a viral sialidase that cleaves the sialic acid from the oligosaccharides
displayed on the surface of the host cell. After these sialic residues are removed the virus can depart
and find a new host for replication. Both Tamiflu and Relenza are inhibitors of the viral
neuraminidase, thus blocking the release of new flu viruses.

Briefly explain the procedure involved in using an oligosaccharide microarray to identify the binding
specificity for a potential lectin.
Ans: First, one synthesizes as many different oligosaccharides as possible and attaches them to
known specific locations on a glass slide in micro-droplets. One then takes a potential lectin
(fluorescently labeled) and passes it over the glass slide. After performing some selectivity washes,
one looks for fluorescently labeled spots that show to which oligosaccharides the lectin has bound.
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Multiple Choice Questions

2. Monosaccharides and disaccharides

3. Monosaccharides and disaccharides

4. Monosaccharides and disaccharides

A) one is a pyranose, the other a furanose.

5. Monosaccharides and disaccharides

A) D-glucose and D-glucosamine

6. Monosaccharides and disaccharides

A) D-glucose and D-fructose

7. Monosaccharides and disaccharides

8. Monosaccharides and disaccharides

A) D-glucose and D-fructose

9. Monosaccharides and disaccharides

10. Monosaccharides and disaccharides

11. Monosaccharides and disaccharides

12. Monosaccharides and disaccharides

13. Monosaccharides and disaccharides

14. Monosaccharides and disaccharides

A) C-4 of glucose is joined to C-1 of galactose by a glycosidic bond.

A) Amylose is unbranched; amylopectin and glycogen contain many (1 → 6) branches.

A) Glycogen forms more internal H-bonds than cellulose.

A) The glycogen sample is more soluble than the cellulose sample.

20. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

21. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

22. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

A) asparagine, serine, or threonine.

23. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

24. Carbohydrates as informational molecules: the sugar code

25. Carbohydrates as informational molecules: the sugar code

26. Carbohydrates as informational molecules: the sugar code

27. Working with carbohydrates

A) Oligosaccharides are often branched.

28. Working with carbohydrates

Short Answer Questions

30. Monosaccharides and disaccharides

31. Monosaccharides and disaccharides

(a) (b) (c) (d) (e)

32. Monosaccharides and disaccharides

33. Monosaccharides and disaccharides

34. Monosaccharides and disaccharides

35. Monosaccharides and disaccharides

36. Monosaccharides and disaccharides

37. Monosaccharides and disaccharides

46. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

47. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

48. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

Ans: A proteoglycan aggregate is a supramolecular assembly of proteoglycan monomers. Each

49. Glycoconjugates: proteoglycans, glycoproteins, and glycolipids

50. Carbohydrates as informational molecules: the sugar code

92 Chapter 7 Carbohydrates and Glycobiology

Pages: 269–270 Difficulty: 3

51. Carbohydrates as informational molecules: the sugar code

52. Carbohydrates as informational molecules: the sugar code

53. Working with carbohydrates

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