CHAPTER SEVEN

CARBOHYDRATES

1. Which of the following is not a carbohydrate?

A)

B)

C)

D)

E)

Ans B

2. Which of the following carbohydrates does not belong to the family of naturally
occurring sugars?

A)
B)

C)

D)

E)

Ans D

3. The compound

is an epimer of which of the following molecules?

A)
B)

C)

D)

E)

Ans A

4. Which of the following structures is the -anomer of D-glucose?

A)

B)
C)

E)

Ans B

5. Which of the following is a -lactone?

A)

B)

C)
D)

E)

Ans C

6. Which of the following is an aldonic acid?

A)

B)

C)

D)

E)
Ans B

7. Which of the following compounds is an aldaric acid?

A)

B)

C)

D)

E)
Ans E

8. Which of the following is an alditol?

A)

B)

C)

D)

E)

Ans E

9. Which of the following is a glycoside?

A)
B)

C)

D)

E)

Ans B

10. Which of the following carbohydrates is a nonreducing sugar?

A) Glucose
B) Fructose
C) Lactose
D) Sucrose
E) Ribose

Ans D

11. The preferred energy source of the brain is __________.

A) fructose
B) glucose
C) arabinose
D) maltose
E) sucrose
Ans B

12. The two most common deoxy sugars are deoxyribose and __________.

A) L-fucose
B) deoxyglucose
C) deoxyarabinose
D) L-sorbose
E) D-sorbose

Ans A

13. Which of the following sugars contains a -1,4-linkage?

A) Cellulose
B) Glucose
C) Amylose
D) Sucrose
E) Maltose

Ans A

14. Oligosaccharides usually contain between __________ and __________ simple sugar
units.

A) 6, 8
B) 2, 10
C) 1, 10
D) 3, 10
E) 7, 10

Ans B

15. Amylopectin is a form of __________.

A) cellulose
B) lactose
C) starch
D) glycogen
E) amylose

Ans C

16. The most abundant organic substance on earth is __________.

A) starch
B) cellulose
C) sucrose
D) glucose
E) Both B and D are correct.

Ans B

17. Which of the following is not a homoglycan?

A) Cellulose
B) Glycogen
C) Starch
D) Heparin
E) Amylose

Ans D

18. Which of the following polysaccharides can bind exceptionally large amounts of
water?

A) Cellulose
B) Glycogen
C) Starch
D) Heparin
E) Amylose

Ans D

19. Carbohydrate is thought to enhance the stability of protein molecules by __________.

A) changing the protein’s shape to better resist denaturation

B) protecting the underlying protein from the action of proteolytic enzymes
C) using hydrogen bonding to increase the stability of the protein
D) Both A and B are correct.
E) All the above are correct.

Ans B

20. In glycoproteins carbohydrate is most often linked to threonine, asparagine or

__________.

A) serine
B) lysine
C) valine
D) aspartic acid
E) tyrosine

Ans A

21. Cellulose is indigestible to most animals because __________

A) cellulose is not soluble in water

B) animals lack the enzymes required to hydrolyze the  links of the cellulose
C) cellulose has no food value and therefore cannot be digested
D) Both A and B are correct.
E) None of the above are correct.

Ans B

22. A glycosidic link is chemically an __________.

A) ether
B) ester
C) amide
D) aldehyde
E) ketone

Ans A

23. Which of the following yields N-acetyl-D-glucosamine on hydrolysis?

A) Cellulose
B) Heparin
C) Chitin
D) Amylopectin
E) Amylose

Ans C

24. Glycoproteins lack which of the following groups typically found in proteoglycans?

A) Uronic acids
B) Sulfate groups
C) N-Glycosidic linkages
D) Both A and B are correct.
E) All of the above are correct.

Ans D

25. Glycogen is __________.

A) the main energy storage molecule of animals
B) the main carbohydrate reserve of animals
C) the main carbohydrate found in seeds
D) a form of plant starch
E) Both C and D are correct.

Ans B

26. Lactose intolerance arises from __________.

A) bacteria in the intestine that produce toxic metabolites

B) the inability of intestinal enzymes to cleave the lactose
C) a sensitivity to galactose
D) a sensitivity to glucose
E) an allergic reaction to glucose

Ans B

27. Glycoconjugates result from the covalent linkage of carbohydrate to proteins or

__________.

A) amino acids
B) lipids
C) nucleotides
D) Both A and B are correct.
E) None of the above are correct.

Ans B

28. The three most common homoglycans found in nature are cellulose, starch, and
__________.

A) amylose
B) lactose
C) fructose
D) glycogen
E) sucrose

Ans D

29. The two polysaccharides used to store glucose as an energy reserve are starch and
__________.

A) glycogen
B) cellulose
C) fructose
D) sucrose
E) maltose

Ans A

30. The principal structural carbohydrate of plants is __________.

A) starch
B) glycogen
C) cellulose
D) amylose
E) xylulose

Ans C

31. The accumulation of AGEs is linked to which of the following diseases?

A) Atherosclerosis
B) Arthritis
C) Diabetes
D) Both A and B are correct.
E) All of the above are correct.

Ans E

32. N-Glycans are linked via a(n) __________ link between the carbohydrate and the
amino acid.

A) -Glycosidic
B) -Glucosidic
C) ester
D) amide
E) Both A and B are correct.

Ans B

33. Which of the following is not a common sugar found in N-glycans?

A) Mannose
B) Glucose
C) Maltose
D) Fucose
E) Galactose

Ans C
34. Which of the following is an example of posttranslational modification of proteins?

A) Phosphorylation
B) Acetylation
C) Proteolytic cleavage
D) Glycosylation
E) All of the above are examples of posttranslational modification.

Ans E

35. The glycome is the __________.

A) total set of sugars and glycans that an organism produces

B) total set of sugars that an organism produces
C) total set of glycans that an organism produces
D) glycoforms produced by a single sugar
E) None of the above are correct.

Ans A

36. The production of the glycan components of each type of glycoprotein as a series of
slightly different forms is referred to as __________

A) glycoformation
B) glycolation
C) microheterogeneity
D) posttranslational modification
E) alternative splicing

Ans C

37. Translation of the sugar code requires which of the following?

A) Glycoforms
B) Lectins
C) RNA
D) DNA
E) Integrins

Ans B

38. How many stereoisomers are possible for an aldohexose?

A) 4
B) 8
C) 12
D) 16
E) 32

Ans D

39. Reaction of an amino acid with C1 of a cyclic aldose produces which of the following
linkages?

A) Ester
B) Amide
C) Glycosidic
D) Imine
E) Schiff base

Ans C

40. Which of the following terms is not associated with glycation reactions?

A) AGEs
B) Amadori products
C) Adduct
D) Lactose
E) Maillard reaction

Ans D

41. The principle means of protection of plants against herbivores is __________.

A) taste
B) smell
C) poison
D) mimicry
E) color

Ans A

42. Of the following primary types of taste perception which is the most important in
identifying calorie-dense foods?

A) Sweet
B) Savory
C) Sour
D) Salty
E) A and B are correct.

Ans A
43. Savory taste detects which of the following?

A) Sugars
B) Amino acids
C) Toxicity
D) Electrolytes
E) Acids

Ans B

44. Glycomics is defined as __________.

A) the investigation of the structure and function of all glycans in a cell.

B) glycosidology
C) glycology
D) lipology
E) saccariology

Ans A

45. In an aldohexopyranose how many methyl groups will be incorporated on treatment

with methyl iodide?

A) One
B) Two
C) Three
D) Four
E) Five

Ans E

46. Which of the following sugars lacks a chiral center?

A) Glucose
B) Glyceraldehyde
C) Dihydroxyacetone
D) Ribose
E) Fructose

Ans C

SHORT ANSWER
47. Define the term diastereomers.

Ans Diastereomers are non-superimposable nonmirror image stereoisomers.

48. What is an enediol?

Ans An enediol is the intermediate formed during the reversible isomerization of sugars
that results in an intermolecular shift of a hydrogen atom and a relocation of a double
bond.

49. What is a reducing sugar?

Ans A reducing sugar is a sugar that can be oxidized by a weak oxidizing agent.

50. What structural relationship is indicated by the term D-sugar?

Ans In D-family sugars, the OH on the chiral carbon farthest from the carbonyl group is
on the right side in a Fischer projection formula. So both (+)-glucose and (−)-fructose are
D-sugars despite their rotation of plane-polarized light in opposite directions.

51. What is the difference between a heteroglycan and a homoglycan? Give an example
of each.

Ans Heteroglycans can be made up of more than one type of monosaccharide residue but
homoglycans contain only one type. Examples of homoglycans and heteroglycans are
starch and hyaluronic acid, respectively.

52. What is a function of glycogen?

Ans Glycogen is a storage form of glucose.

53. The polymer chains of glycosaminoglycans are widely spread apart and bind large
amounts of water. What functional groups of the polymer are responsible for this
phenomenon?

Ans GAGs are widely spread apart and attract large amounts of water because of charge
repulsion caused by negatively charged and hydrophilic sulfate and carboxylate groups.

54. What role do carbohydrate groups play in maintaining glycoprotein stability?

Ans Numerous carbohydrate groups protect glycoproteins from denaturation because

they are hydrophilic groups that surround the protein and protect against protease-
catalyzed peptide bond cleavage.

55. What are function of proteoglycans?

Ans Proteoglycans provide strength, support, and elasticity to tissue.

56. Classify D-glyceraldehyde and dihydroxyacetone as enantiomers, diastereomers,

epimers or an aldose-ketose pair.

Ans Glyceraldehyde and dihydroxyacetone phosphate are an aldose-ketose pair.

57. Classify D-glucose and D-mannose as enantiomers, diastereomers, epimers, or an

aldose ketose pair.

Ans D-glucose and D-mannose are epimers.

58. Raffinose, the most abundant trisaccharide in nature, occurs in whole grains and
numerous vegetables. It is the -galactosyl derivative of sucrose. Is raffinose a reducing
or nonreducing sugar?

Ans Raffinsoe is a reducing sugar because the galactosyl ring can open.

59. Define the term reducing sugar. What structural feature does a reducing sugar have?

Ans A reducing sugar reduces Cu(II) in Benedict’s reagent. This reduction takes place
because the hemiacetal portion of a sugar can form an aldehyde functional group, which
can be oxidized to a carboxylic acid.

60. What structural differences characterize cellulose, glycogen and starch?

Ans Amylopectin, at type of starch and glycogen are both homoglycans containing
glucose monomers linked by α-(1,4) glycosidic bonds with branch points connected by α-
(1,6) glycosidic bonds. Glycogen, however, is much more highly branched than
amylopectin. Cellulose is a linear polymer of glucose linked by β-(1,4) glycosidic bonds.

61. Phosphate esters can form at position 2 to 6 of an aldohexose but not in position 1.
Explain.

Ans Phosphate esters can form at positions 2–6 of an aldohexose because all these
carbons bear alcoholic OH groups. In contrast, a phosphate at the anomeric carbon would
be a mixed anhydride.

62. Suggest a reason why sorbitol prevents water loss in candy.

Ans Moisture loss is prevented because of hydrogen bonding between the OH groups of
sorbitol and water.

63. What sugar is produced by the epimerization of galactose?

Ans Three sugars are possible. Talose is the sugar produced by the epimerization of
galactose at C2. The C4 epimer is glucose, and the C3 epimer is galactose.

64. Sucrose does not undergo mutarotation. Explain.

Ans In order for the sugar to undergo mutarotation there must be a hemiacetal or
hemiketal as part of the structure. Sucrose’s anomeric carbons are linked in a full acetal
linkage.

65. Treatment of fructose with methyl iodide produces 1,3,4,6,-tetra-O-methylfructose

What does this information tell you about the ring structure of fructose?

Ans The information provided reveals that the fructose molecule has a five-membered
ring since the hydroxyl at carbon six is methylated.

66. Why is it advantageous for a plant toxin to elicit a bitter taste when an animal eats the
plant rather than a bland or sweet taste?

Ans A bitter taste is sufficiently unpleasant that the animal will immediately make the
connection between the type of plant and the unpleasant sensation. As a result the animal
will stop eating and then avoid the offending plant in the future. If the toxin’s taste is
neutral or sweet sufficient time may elapse between consuming the toxin and the onset of
any unplesant effects. The animal may continue to eat the plant, thereby defeating the
toxin’s purpose.

67. How does glycosylation improve the water solubility of a water-insoluble molecule?

Ans The OH groups of the sugar interact with the water via hydrogen bonding to improve
the solubility of the entire molecule.

ESSAY QUESTIONS

68. Toxic compounds in plants frequently have bitter tastes that are detectable at very low
concentrations. The sweet taste of carbohydrates is only detectable at much higher levels.
Can you suggest a reason why this is true?

Ans Certain plants contain toxic molecules that protect them from foraging animals. It is
therefore highly desirable for animals to detect plant toxins at very low levels. Sweet
taste is a signal that food is rich in calories and is not toxic. A higher detection limit for
sweet taste assures consumption of only those foods that have a high caloric content.

69. The simplest chiral aldose has three carbon atoms, but the simplest chiral ketose has
four carbons. Explain. Include structures in your answer.

Ans Chiral molecules must have a carbon center bearing four different groups. This is
possible for a three carbon aldehyde where the carbonyl is at the end of the chain. In a
ketose the carbonyl is in the body of the chain and can therefore only possess a chiral
carbon center when the molecule has at least four carbons.

Aldotriose Ketotetrose

70. Normally, the formation of an acetal requires the incorporation of two alcohol units.
Formation of a sugar acetal requires only the incorporation of one additional molecule of
alcohol. Explain.

Ans A sugar is actually a polyalcohol that forms a cyclic hemiacetal when one of these
sugar alcohol groups is used. Acetal formation requires that one additional alcohol unit
react with the cyclic hemiacetal.

71. 1-Methylglucose is a nonreducing sugar, whereas 2-methylglucose is a reducing

sugar. Explain.

Ans The methyl group in 1-methylglucose is part of a full acetal which is not capable of
acting as a reducing sugar. Since 2-methylglucose has a free aldehyde group it is capable
of acting as a reducing sugar.

72. How does glycation of red blood cells serve as a measure of long term blood glucose
levels?

Ans The amino groups of hemoglobin within red blood cells form covalent bonds with
sugar molecules. Since this is a nonenzymatic process it takes time. Glycated hemoglobin
levels therefore are an indicator of blood glucose control over an extended period of time.

73. What is the smallest ketose that can form a stable ring?

Ans Stable ketose rings contain five or greater atoms, one of which is an oxygen. Since
the ketone group must be at least one carbon in from the end of the chain a ketopentose
would be the smallest ketose capable of forming a stable ring.

74. Five- and six-membered ring carbohydrate hemiacetals and hemiketals are reasonably
stable and can be easily isolated in contrast to a typical organic acetal. Account for this
difference in stability.
Ans Carbohydrate acetals have an OH in close proximity to the carbonyl group and easily
form a five or six membered rings. This is not true of simple aldehydes and ketones.

75. Polysaccharides can form stable gels that contain immobilized water. How does the
polysaccharide immobilize the water?

Ans The many OH groups of the polysaccharide interact with water molecules through
hydrogen bonding. Hydrogen bonds can be formed between a single water molecule and
several carbohydrate groups effectively immobilizing the polymer.

76. There are two chemically distinct forms of glucose. How is it possible for a single
molecule to behave as two distinct molecules?

Ans Glucose can form a ring and in so doing generate a new chiral center. The two ring
forms of the glucose that can form the straight chain molecule are diastereomers
(nonsuperimposable nonmirror image stereoisomers) and as such have distinct chemical
and physical properties.