Chapter 10 Carbohydrates

Matching Questions
Use the following to answer questions 1-10:

Choose the correct answer from the list below. Not all of the answers will be used.
a) Fehling’s
b) enantiomers
c) UDP
d) glycogen
e) monosaccharides
f) cellulose
g) lectins
h) heparin
i) axial
j) glycoproteins
k) epimers
l) glycosyltransferases

1. ____________ This class of compounds has the molecular formula CH2On.

Ans:
Section: Introduction

2. ____________ These are stereoisomers that are mirror images of one other.

Ans:
Section: 10.1

3. ____________ These monosaccharides differ at a single asymmetric carbon.

Ans:
Section: 10.1

4. ____________ This is one of the most abundant organic molecule in the biosphere.

Ans:
Section: 10.2

5. ____________ This is a test solution used to identify reducing and nonreducing sugars.

Ans:
Section: 10.1

6. ____________ This is the storage form of glucose in animals.

Ans:
Section: 10.2
Chapter 10 Carbohydrates 2

7. ____________ This is an example of a glycosaminoglycan.

Ans:
Section: 10.3

8. ____________ These are the enzymes that synthesize oligosaccharides.

Ans:
Section: 10.2

9. ____________ These are molecules to which most sugars are attached prior to transfer.

Ans:
Section: 10.2

10. ____________ These proteins bind to specific carbohydrate structures.

Ans:
Section: 10.4

Fill-in-the Blank Questions

11. A is a stereoisomer that is not a mirror image.
Ans: Section: 10.1

12. A is a five-membered ring formed from a monosaccharide.

Ans: Section: 10.1

13. A is formed when two monosaccharides are linked together via a glycosidic bond.
Ans: Section: 10.2

14. Plant starch is composed of amylose, a linear polymer of glucose, and a branched polymer of
glucose referred to as .
Ans: Section: 10.2

15. Maltose is composed of two molecules of glucose linked together by a glycosidic bond.
Ans: Section: 10.2

16. is a galactose joined to a glucose by a β-1,4 glycosidic bond.

Ans: Section: 10.2

17. In N-linked glycoproteins, the carbohydrate portion is attached to a(n) residue in the protein.
Ans: Section: 10.3

18. When the carbohydrate portion is attached to a serine or threonine residue in a glycoprotein, it is
referred to as a(n) glycoprotein.
Ans: Section: 10.3
Chapter 10 Carbohydrates 3

19. The influenza virus recognizes residues of glycoproteins present on cell surfaces.
Ans: Section: 10.4

20. Repeating units in have a least one negatively charged carboxylate or sulfate group.
Ans: Section: 10.3

Multiple-Choice Questions
21. Carbohydrates are:
A) aldehydes with two or more hydroxyl groups.
B) ketones with two or more hydroxyl groups.
C) acids with two or more hydroxyl groups.
D) alcohols with two or more hydroxyl groups.
E) A and B.
Ans: Section: 10.1

22. The simplest carbohydrates are:

A) D- and L-glyceraldehyde.
B) dihydroxyacetone and D- and L-glyceraldehyde.
C) dihydroxyacetone and glycerate.
D) All of the above.
E) None of the above.
Ans: Section: 10.1

23. An aldehyde and alcohol can react to form a:

A) hemialkyl. D) All of the above.
B) hemiketal. E) None of the above.
C) hemiacetal.
Ans: Section: 10.1

24. Fructose can cyclize to (a):

A) pyranose ring.
B) furanose ring.
C) both pyranose and furanose ring forms.
D) All of the above.
E) None of the above.
Ans: Section: 10.1

25. The nutritional storage form(s) of glucose in plants.

A) glycogen B) amylose C) amylopectin D) B and C. E) All of the above.
Ans: Section: 10.2

26. Which enzyme digests amylopectin?

A) -amylase D) All of the above.
B) amylose E) None of the above.
C) cellulose
Ans: Section: 10.2
Chapter 10 Carbohydrates 4

27. To which amino acid residues in glycoproteins are the sugars commonly linked?
A) tyrosine and asparagine D) serine and threonine
B) serine, threonine, and asparagine E) A and D.
C) serine, tyrosine, and asparagine
Ans: Section: 10.3

28. Glycoproteins are normally:

A) found on membranes. D) A and B.
B) secreted as extracellular proteins. E) All of the above.
C) found inside organelles.
Ans: Section: 10.3

29. All of the following are repeating units of glycosaminoglycans except:

A) chondroitin 6-sulfate. D) heparin.
B) keratin sulfate. E) All of these form glycosaminoglycans.
C) hyaluronate.
Ans: Section: 10.3

30. Which of the following is the anomer of β-D-glucopyranose?

A) CH2OH C) CH2OH CH2OH
E)
OH O OH O O OH
OH OH OH OH
OH OH OH
OH OH
B) CH2OH
D)
O CH2OH OH
O
OH OH
OH OH
OH OH
Ans: Section: 10.2

31. All of the following are thought to play a role in cancer prevention except:
A) glucosinolates that are formed by the condensation of glucose with an organic
isothiocyanate.
B) plants of the order Brassicales hydrolyze glucosinolates and that store organic
isothiocyanates as a defense against herbivory.
C) organic isothiocyanates that have a mustard-oil flavor.
D) Brassicales, which include mustard, relish, kale, and broccoli.
E) in humans, glucosinolates that stimulate the production of detoxifying enzymes.
Ans: Section: 10.2

32. Selectins are proteins that:

A) selectively bind proteins destined for lysozomes.
B) aid in selection of proteins bound for the Golgi complex.
C) bind immune-system cells as part of the inflammatory response.
D) All of the above.
E) None of the above.
Ans: Section: 10.4
Chapter 10 Carbohydrates 5

33. What are lectins?

A) proteins that bind the carbohydrates on glycoproteins and other macromolecules
B) proteins that promote cell-cell interaction
C) proteins found in animals, plants, and microorganisms
D) All of the above.
E) None of the above.
Ans: Section: 10.4.

34. How do some viruses gain entry into specific cells?

A) by attaching to ion channels
B) by cleaving the glycosidic bonds and altering protein shapes
C) by binding to glycoproteins on the cell surface that are unique to specific cells
D) All of the above.
E) None of the above.
Ans: Section: 10.4

35. Inhibitors against which viral enzyme have potential as anti-influenza agents?
A) calnexin D) All of the above.
B) neuramidase E) None of the above.
C) selectin
Ans: Section: 10.4

36. How do some viruses gain entry into specific cells?

A) by attaching to ion channels
B) by cleaving the glycosidic bonds and altering protein shapes
C) by binding to glycoproteins on the cell surface that are unique to specific cells
D) All of the above.
E) None of the above.
Ans: Section: 10.4

37. Biochemists organize proteins with carbohydrates attached into three classes. Below is a list of
structural differences in these three classes, one of which is assigned to the wrong class. Identify
the incorrect structural correlation.
A) Unlike glycoproteins and proteoglycans, in mucopolysaccharides carbohydrates are
attached via ester bonds to Asp and Glu.
B) The glycosaminoglycan component of proteoglycans determines their properties.
C) The defining feature of the mucopolysaccharide is a region of the protein backbone called
the variable number of tandem repeats region.
D) The carbohydrate portion of glycoproteins such as erythropoietin are thought to make it
more soluble in blood.
E) Glycosaminoglycans often have repeating units of disaccharides containing a negatively
charged carboxylate or sulfate group.
Ans: Section: 10.3
Short-Answer Questions
38. List some of the reasons carbohydrates are considered important molecules.
Ans: Carbohydrates serve several important functions as fuels, metabolic intermediates, and
energy stores. They are the basis of most of the organic matter on our planet.
Carbohydrates serve as the structural framework or building blocks for DNA, RNA, and
polysaccharides. They are also linked to other molecules, such as proteins and lipids, and
Chapter 10 Carbohydrates 6

play important roles in signaling and structure.

Section: Introduction

39. Draw the Fischer projection structures of all of the trioses.

Ans: O O
CH2OH C H
C H
C O HO C H
H C OH
CH2OH CH2OH
CH2OH
dihydroxyacetone D-glyceraldehyde L-glyceraldehyde
Structures shown on page 168.
Section: 10.1

40. What is the difference between an enantiomer and a diastereoisomer?

Ans: An enantiomer is a stereoisomer that is a perfect (nonsuperimposable or nonidentical)
mirror image. A chiral molecule has one perfect mirror image. But for larger
carbohydrates that have the same chemical formula and have multiple chiral centers,
variations in asymmetric carbon structures mean that additional stereoisomers exist. The
stereoisomers that are not mirror images of each other are called diastereoisomers.
Section: 10.1

41. How is the D or L configuration determined in carbohydrates?

Ans: The D or L designation is determined by the asymmetric carbon farthest from the ketone
or aldehyde group, and is related to the glyceraldehyde D and L structures.
Section: 10.1

42. Draw the Haworth projections of the two pyranose forms of D-glucose.
Ans: CH2OH CH2OH
O O OH
OH OH
OH OH OH
OH OH
α-D-glycopyranose β-D-glucopyranose
Shown in Figure 10.3 of the text.
Section: 10.1

43. Draw the structure of lactose. Identify the monosaccharides involved and identify the type of
linkage in lactose?
Ans: D-glucose ( anomer)
CH2OH
D-galactose O
CH2OH OH
OH O O OH
OH OH

OH  1-4 glycosidic linkage

Chapter 10 Carbohydrates 7

Section: 10.2

44. Compare the structures of amylopectin and amylose.

Ans: Both are homopolymers of glucose. Amylose consists of unbranched -1,4 linkages of
glucose. Amylopectin is a branched structure, and contains both -1,4 linkages and -1,6
linkages, with the -1,6 branches occurring about once every 30 glucose residues.
Section: 10.2

45. What are the chemical, structural, and functional differences between cellulose and glycogen?
Ans: Both are glucose homopolymers. Glycogen is a branched polymer and contains -1,4
linkages with -1,6 branchpoints about every 10 residues. Glycogen is the polymeric
form of glucose in animals with a tertiary structure of open helices. This makes glycogen
a more compact, accessible glucose store. Cellulose is a linear polymer that contains -
1,4 linkages. Because of the  linkages, cellulose can form very long straight chains that
can form interchain hydrogen bonds to form fibrils with high tensile strength. Thus,
cellulose is the major structural component of plant cell walls and is an important source
of dietary fiber in animals.
Section: 10.2

46. Describe some of the functions of glycosaminoglycans and proteoglycans.

Ans: They function as lubricants, anticoagulents, and structural components; are important in
pathways stimulating cell proliferation; and aid in mediating cell adhesion to extracellular
matrices.
Section: 10.3

47. How does a genetic mutation account for some of the different human blood types?
Ans: Blood type is determined by specific glycosyltransferases that add the end sugar to the
glycoproteins found on red blood cells. Three different types of glycosyltransferase genes
can be inherited, and each individual receives one from each parent. Two different forms
result in the A and B blood types. A mutation in a third type results in a truncated product
that is not active.
Section: 10.3

48. What is the advantage of having different blood types within a species?
Ans: Variations are protective because differences may be critical to protection against disease
and infection. A microorganism that gains advantage over a host by mimicking and/or
using specific antigens, will not survive in host members that have differing antigens.
Section: 10.3

49. What are some of the defining characteristics of mucins?

Ans: The protein portion of the mucin has a region called VNTR (variable number of high
repeats) to which the carbohydrate attaches. This VNTR region is flanked by a cis rich
region.
Section: 10.4

50. What are the two primary functions of the Golgi complex?
Ans: The Golgi complex is 1) the site of carbohydrate addition and modification to
glycoproteins, and 2) the major protein-sorting center of the cell.
Section: 10.3
Chapter 10 Carbohydrates 8

51. What are selectins and how do they facilitate development?

Ans: Selectins are a class of lectins, some of which promote cell-to-cell contact in the immune
system response to injury. Others promote the recognition and attachment of embryos to
the endometrial wall of the mother’s uterus.
Section: 10.4

52. Which tissues synthesize mucins and why?

Ans: Mucins are synthesized by tracheobronchial, gastrointestinal, and urogenital tract cells.
The key function of mucins is to act as a lubricant needed to move large insoluble
particles through these systems.
Section: 10.3

53. Your grandfather tells you that his doctor is now measuring A1c (a form of hemoglobin) levels
to check his diabetes. Your grandfather is confused as to why his doctor would check levels of a
protein (hemoglobin) to monitor blood carbohydrate (glucose) levels. What do you tell him?
Ans: Explain to your grandfather that high levels of glucose in the blood can react with
hemoglobin to form an altered form of hemoglobin called glycosylated hemoglobin or
HbA1c.This is because a small percentage of those glucose molecules are in a form called
reducing sugars, a more reactive form of glucose. Blood glucose tests give an
instantaneous measure of the amount of glucose in the blood, whereas the A1c test
measures the average blood glucose levels over time. The more glucose that is attached to
hemoglobin, the worse the blood sugar control.
Section: 10.1