Chapter 4: Amino Acids

Matching
A)
B)
C)
D)
E)
F)
G)
H)
I)
J)
K)
L)
M)
N)
O)
P)

glutamate
uncharged
deprotonated
three
amino group
two
C-terminus
lysine
racemic mixture
cysteine
zero
protonated
isoleucine
tryptophan
phenylalanine
N-terminus

1. The net charge of the zwitterion form of Gly is ______.

Ans: K
Section: 4.1.A
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
2. When a peptide bond is formed, an ______ reacts with a carboxylate group.
Ans: E
Section: 4.1.B
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
3. At a pH above its pKa, the phenol group of tyrosine is ______.
Ans: C
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

4. In the tripeptide LysProIle, there are ______ charged groups at pH 7.

Ans: D
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
5. At a pH below its pKa, the -amino group of lysine is ______.
Ans: L
Section: 4.1.D
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
6. At a pH below its pKa, the -carboxylate group of Asp is ______.
Ans: B or L
Section: 4.1.D
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
7. In the peptide TrpSerVal, valine is at the ______.
Ans: G
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
8. In the tripeptide TrpValPhe, the N-terminal residue is ______.
Ans: N
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
9. In the tripeptide LysProIle, the C-terminal residue is _________.
Ans: M
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

10. Biological systems usually produce a single enantiomer, whereas chemical synthesis
produces a ______.
Ans: I
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry
11. GABA is a neurotransmitter derived from ______.
Ans: A
Section: 4.3.B
Level of Difficulty: Easy
Learning objective: Amino Acid Derivatives
12. Glutathione is a tripeptide containing a central ______ residue.
Ans: J
Section: 4.3.B
Level of Difficulty: Easy
Learning objective: Amino Acid Derivatives

Multiple Choice
13. In the early 1930s William Rose fed laboratory rats a mixture of all 19 amino acids known
to be present in proteins. He observed that his rats lost weight. This observation led to the
discovery of ______ as the 20th amino acid found in proteins.
A) Gly
B) Ala
C) Tyr
D) Asn
E) Thr
Ans: E
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
14. What percentage of the 20 amino acids is considered to be nutritionally essential to lab
animals?
A) 0%
B) 25%
C) 50%
D) 75%
E) 100%
Ans: C
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
15. About half of the 20 amino acids are called essential because
A) they are essential for the synthesis of pyrimidines.
B) they are essential for the synthesis of purines.
C) they are essential for nitrogen metabolism.
D) our bodies need them for protein synthesis.
E) our bodies cannot synthesize them and therefore they need to be present in our diet.
Ans: E
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

16. Which amino acid does not have a primary -amino group?
A) glutamine
B) arginine
C) lysine
D) proline
E) glutamate
Ans: D
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
17. Which of the following statements is true?
A) Amino acids can be derived from purines.
B) Purines and pyrimidines can be derived from amino acids.
C) Corn contains all 20 standard amino acids.
D) Amino acids can be derived from pyrimidines.
E) none of the above
Ans: B
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
18. Which of the following amino acids is the least abundant in proteins?
A) V
B) W
C) G
D) F
E) A
Ans: B
Section: 4.1
Level of Difficulty: Difficult
Learning objective: Amino Acid Structure

19. Zwitterions are

A) amino acids.
B) ionic molecules that are racemic.
C) ions that bear both negatively and positively charged groups.
D) side chain carboxylate anions.
E) delocalized ions.
Ans: C
Section: 4.1.A
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
20. The formation of a dipeptide from two amino acids involves
A) side-chain complementarity.
B) loss of water.
C) oxidation of the -carbon.
D) reduction of the -carbon.
E) base catalysis.
Ans: B
Section: 4.1.B
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

21. The diagram below shows

A)
B)
C)
D)
E)

an amino acid.
a dipeptide.
a tripeptide.
a tetrapeptide.
a polypeptide.

Ans: D
Section: 4.1.B
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
22. Which of the following amino acids has a charged polar side chain at pH 7.0?
A) Leu
B) Ala
C) Met
D) Trp
E) Glu
Ans: E
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

23. Which of the following tripeptides carries a net positive charge at pH 7.0?
A) AlaThrAsn
B) GlnValSer
C) ArgGluMet
D) ProIleLeu
E) LeuLysGly
Ans: E
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
24. Which of the following amino acids has a sulfur atom in its side chain?
A) Asn
B) Ser
C) Phe
D) Met
E) Tyr
Ans: D
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
25. Which of the following amino acids does not have an ionizable side chain?
A)
B)
C)
D)
E)

Asp
Cys
Lys
His
Asn

Ans: E
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

26. Which of the following amino acids has an uncharged polar side chain at pH 7.0?
A) Arg
B) Thr
C) Glu
D) Pro
E) Ile
Ans: B
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
For questions 27 and 28 refer to the diagram below

27. What is the three-letter symbol for the amino acid shown above?
A) Ala
B) Asn
C) Gln
D) Asp
E) Glu
Ans: B
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

28. The ionization of amino acids depends on the pH and the pKas of the ionizable groups. The
pK1 and pK2 for the amino acid shown above are 2.1 and 8.8, respectively. At what pH is the
amino acid ionized predominantly as shown?
A) pH 1.0
B) pH 2.1
C) pH 5.5
D) pH 8.8
E) pH 10.0
Ans: A
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
29. The pK1, pK2, and pKR for the amino acid arginine are 1.8, 9.0, and 12.5, respectively. At
pH 7.0 arginine would be charged predominantly as follows:
A) -carboxylate 0, -amino 0, guanidino +1, net charge +1
B) -carboxylate +1, -amino 0, guanidino -1, net charge 0
C) -carboxylate +1, -amino 1, guanidino 1, net charge 1
D) -carboxylate 1, -amino +1, guanidino +1, net charge +1
E) -carboxylate 1, -amino 0, guanidino +1, net charge 0
Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
30. The pK1, pK2, and pKR for the amino acid aspartic acid are 2.0, 9.9, and 3.9, respectively. At
pH 7.0, aspartic acid would be charged predominantly as follows:
A) -carboxylate 0, -amino +1, -carboxylate 0, net charge +1
B) -carboxylate 1, -amino +1, -carboxylate 1, net charge 1
C) -carboxylate 0, -amino 1, -carboxylate 0, net charge 1
D) -carboxylate +1, -amino 1, -carboxylate +1, net charge +1
E) -carboxylate +1, -amino +1, -carboxylate +1, net charge +3
Ans: B
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

10

31. The pK1, pK2, and pKR for the amino acid glutamate are 2.1, 9.5, and 4.1, respectively. At
pH 11.0, glutamate would be charged predominantly as follows:
A) -carboxylate +1, -amino 0, -carboxylate +1, net charge +2
B) -carboxylate 1, -amino +1, -carboxylate 1, net charge 1
C) -carboxylate 0, -amino 0, -carboxylate 0, net charge 0
D) -carboxylate +1, -amino 1, -carboxylate +1, net charge +1
E) -carboxylate 1, -amino 0, -carboxylate 1, net charge 2
Ans: E
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
32. The pK1, pK2, and pKR for the amino acid histidine are 1.8, 9.3, and 6.0, respectively. At pH
4.0 would be charged predominantly as follows:
A) -carboxylate +1, -amino 0, imidazole 1, net charge 0
B) -carboxylate 1, -amino +1, imidazole 0, net charge 0
C) -carboxylate +1, -amino +1, imidazole 1, net charge +1
D) -carboxylate 1, -amino +1, imidazole +1, net charge +1
E) -carboxylate 0, -amino +1, imidazole +1, net charge +2
Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
33. The pK1, pK2, and pKR for the amino acid cysteine are 1.9, 10.7, and 8.4, respectively. At pH
5.0, cysteine would be charged predominantly as follows:
A) -carboxylate 0, -amino 0, sulfhydryl 0, net charge 0
B) -carboxylate +1, -amino 1, sulfhydryl 1, net charge 1
C) -carboxylate 1, -amino +1, sulfhydryl +1, net charge +1
D) -carboxylate 1, -amino +1, sulfhydryl 0, net charge 0
E) -carboxylate +1, -amino 1, sulfhydryl 0, net charge 0
Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

11

34. The pK1, pK2, and pKR for the amino acid lysine are 2.2, 9.1, and 10.5, respectively. At pH
1.0, lysine would be charged predominantly as follows:
A) -carboxylate 0, -amino 1, -amino 1, net charge 2
B) -carboxylate 1, -amino +1, -amino +1, net charge +1
C) -carboxylate +1, -amino +2, -amino +2, net charge +5
D) -carboxylate 0, -amino +1, -amino +1, net charge +2
E) -carboxylate +2, -amino +1, -amino +1, net charge +4
Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
Questions 35-37 are based on the diagram shown below.

35. How many amino acid residues are present in the peptide shown above?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: C
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

12

36. What is the name of the N-terminal amino acid in the peptide shown above?
A) cysteine
B) methionine
C) valine
D) alanine
E) tryptophan
Ans: B
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
37. What is the three-letter symbol for the C-terminal amino acid in the peptide shown above?
A) Gly
B) Asp
C) Tyr
D) Met
E) Phe
Ans: E
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
38. While proteins are usually composed of linear chains of amino acids, branched chains of
amino acids and internally cross-linked chains can be found in certain proteins. Polypeptide
chains are most commonly linked to each other through
A)
B)
C)
D)
E)

hydrogen bonds.
glycosidic bonds.
peptide bonds.
disulfide bonds.
ester linkages.

Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

13

39. The disulfide bond between two cysteine molecules

A) is a peptide bond.
B) is an ionic interaction that is stable at physiological pH.
C) is a covalent bond formed by oxidation.
D) is a hydrogen bond between the two sulfhydryl groups.
E) is a dipole-dipole interaction.
Ans: C
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
40. The two peptides shown in the diagram below are linked through

A)
B)
C)
D)
E)

a hydrogen bond.
a glycosidic bond.
a peptide bond.
a disulfide bond.
an ester linkage.

Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

14

41. Which one of the representations describes the oligopeptide shown below?

A)
B)
C)
D)
E)

Tyr-Ala-Thr
Tyr-Gly-Cys
Tyr-Ala-Ser
Phe-Gly-Cys
Phe-Ala-Thr

Ans: C
Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
42. The tripeptide glycylarginylglutamate contains four ionizable groups with pKas of 2.1, 4.1
9.8, and 12.5. Calculate the pI for this molecule.
A)
B)
C)
D)
E)

3.1
6.4
7.0
7.3
8.3

Ans: C
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

15

43. The tripeptide alanyllysylaspartate contains four ionizable groups with pKas of 2.0, 3.9, 9.9,
and 10.5. Calculate the pI for this molecule.
A) 3.0
B) 6.0
C) 6.2
D) 10.2
E) none of the above
Ans: E
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
44. The isoelectronic point of an amino acid is the point where
A) the pKa of the -carboxylic acid is the same as the pKa of the -amino group.
B) the -carboxylic acid is protonated and the -amino group is unprotonated.
C) the solubility of the amino acid is maximized.
D) the -carboxylic acid and the -amino group are both half protonated.
E) the amino acid carries no net electrical charge.
Ans: E
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
45. The side-chains of amino acids have
A) a positive charge in every situation.
B) pKas that assure the solubility of every protein.
C) constant pKas no matter what aqueous environment they are found in.
D) different pKas in peptides as compared to the free amino acids
E) polar functional groups.
Ans: D
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

16

46. Asx refers to

A) a negatively charged aspartic acid.
B) a positively charged asparagine.
C) a dipeptide containing both aspartic acid and asparagine.
D) either aspartic acid or asparagine.
E) an unnatural amino acid formed during acid hydrolysis of peptide bonds.
Ans: D
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
47. The peptide AYDG has an N-terminal _________ residue.
A) glycine
B) glutamic acid
C) glutamine
D) aspartic acid
E) alanine
Ans: E
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
48. Which of the following tripeptides would be expected to be the most hydrophobic?
A) KYG
B) KYA
C) GYA
D) DYA
E) DYG
Ans: C
Section: 4.1.E
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

17

49. What is the three-letter abbreviation for the peptide valylarginylisoleucine?

A) ValArgIle
B) ValAgnLeu
C) VlnArgIle
D) ValAgnIsl
E) VlnArgLeu
Ans: A
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
50. Ribosomes use L amino acids to synthesize proteins. These amino acids are called L
because
A) they are chiral.
B) they turn polarized light to the left.
C) they have a configuration of groups around the C that can be related to the configuration of
groups around the asymmetric carbon in L-glyceraldehyde.
D) they are all (S)-amino acids.
E) they are all (R)-amino acids.
Ans: C
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry
51. Ribosomes use L amino acids to synthesize proteins. These amino acids are called L
because
A) they are chiral.
B) they turn polarized light to the left.
C) they are all (S)-amino acids.
D) they are all (R)-amino acids.
E) none of the above
Ans: E
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry

18

52. Which of the amino acids represented below has two chiral centers?
A)
B)
C)
D)
E)

Ala
Leu
Ile
Pro
Asn

Ans: C
Section: 4.2
Level of Difficulty: Difficult
Learning objective: Stereochemistry
53. Which of the five amino acids shown below has 2 chiral centers?

Ans: C
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry

19

54. All the standard amino acids except ____ are optically active.
A) Pro
B) Arg
C) Trp
D) Gly
E) Phe
Ans: D
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry
55. The __________ character of most standard amino acids causes solutions of amino acids to
rotate the plane of polarized light.
A) chiral
B) zwitterionic
C) polar
D) hydrophobic
E) none of the above
Ans: A
Section: 4.2
Level of Difficulty: Easy
Learning objective: Stereochemistry
56. All amino acids derived from proteins have the same stereochemical conformation as.
A) L-glyceraldehyde.
B) (R)-alanine.
C) D-glucose.
D) (S)-cysteine.
E) glycine.
Ans: A
Section: 4.2
Level of Difficulty: Moderate
Learning objective: Stereochemistry

20

57. Typically, modified amino acids, those with side chain modifications that are present in
proteins
A) are synthesized due to genetic mutations.
B) are assembled by specialized bacterial enzymes.
C) are formed by modification of standard side chain residues after the protein is synthesized.
D) are toxic.
E) are racemic.
Ans: C
Section: 4.3.A
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives
58. An amide bond between a side-chain carboxylate and an -amino group is also called a(n)
A) disulfide bond.
B) anhydride bond.
C) ester bond.
D) isopeptide bond.
E) glycosidic bond.
Ans: D
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives

21

Questions 59-61 are based on the diagram below.

59. What is the name of this molecule?

A) GABA
B) thyroxine
C) -carboxyglutamate
D) glutathione
E) epinephrine
Ans: D
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives
60. Residues 1 and 2 in the peptide shown above are connected through a
A)
B)
C)
D)
E)

hydrogen bond.
an isopeptide bond.
an ester linkage.
disulfide bond.
a glycosidic bond.

Ans: B
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives

22

61. What is the three-letter symbol of the N-terminal amino acid in the structure shown above?
A)
B)
C)
D)
E)

Asp
Asn
Gln
Glu
Lys

Ans: D
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives

23

Short Answer
62. Glutamine is an amino acid (pKas are 2.2, and 9.1). Draw the predominant structure of
glutamine at pH 1.0.

Ans:
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
63. Glutamic acid is an amino acid (pKas are 2.1, 4.1 and 9.5). Calculate the isoelectric point of
glutamic acid.
Ans: At pH 1.0 glutamic acid has an electric charge of +1, at pH 3.0 the electric charge equal 0,
and at pH 5.0 the electric charge equals 1. Therefore the pKas of the carboxylic acid groups
surround the neutral form. pI = (2.1 + 4.1)/2 = 3.1
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

24

64. Tryptophan is an amino acid (pKas are 2.5, and 9.4).

a.
b.
c.
d.

How many different amino acids can be incorporated into proteins during translation?
Give the three- and one-letter abbreviation for tryptophan.
Draw the predominant structure of tryptophan at pH 7.0.
Calculate the pI of Tryptophan.

Ans: a. 20
b. Trp and W

c.
d. pI = (2.5 + 9.4)/2 = 6.0
Section: 4.1.D
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

25

65. In general, amino acids are chiral molecules that act as building blocks for proteins. In
addition, amino acids and amino acid derivative can act as extracellular messenger molecules
such as hormones or neurotransmitters.
a.
b.
c.
d.

How many different amino acids can be incorporated into proteins during translation?
Do ribosomes use L or D amino acids for protein synthesis?
Name one amino acid or amino acid derivative that can act as hormone or neurotransmitter.
Draw the predominant structure of valine at pH 10 (pKas are 2.3 and 9.7).

Ans: a. 20
b. L
c. glycine, glutamate, -aminobutyric acid (GABA), dopamine, or serotonin

d.
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

26

66. The figure below shows the predominant structure of an oligopeptide at pH 7.0.

a. How many amino acids are present in this peptide?

b. Circle one peptide bond in this peptide.
c. Draw a square around one alpha carbon in this peptide
d. The pKas of the ionizable groups in this peptide are 2.0, 4.0, and 9.0. What is the ionic charge
of this molecule at pH 1.0
e. What is the name of the N-terminal amino acid in this peptide?
Ans: a. 5

b.
c.
d. The charge of this molecule at pH 1.0 is +1. At pH 1.0 all ionizable groups are protonated;
the two carboxylic acid groups are neutral and the amino group is positively charged.
e. aspartate (aspartic acid)
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

27

67. The picture below shows the structure of -amino-butyric acid (GABA).

a. From which amino acid is GABA derived (give the name of the amino acid closest in
structure to GABA).
b. What is the structural difference between GABA and this amino acid.
c. What is the function of GABA.
Ans: a. glutamate
b. GABA is missing the -carboxylic acid group
c. GABA is a neurotransmitter (a chemical that mediates communication between neurons)
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives

28

68. The picture below shows the structure of serotonin.

a.
b.
c.
d.

From which amino acid is serotonin derived?

What are the structural differences between serotonin and this amino acid?
What is the function of serotonin?
Which illness can be caused by reduced levels of serotonin in the brain?

Ans: a. Tryptophan
b. Serotonin has a hydroxyl group attached to the 6-membered ring and it misses the -amino
group.
c. Serotonin is a neurotransmitter
d. Depression
Section: 4.3.B
Level of Difficulty: Moderate
Learning objective: Amino Acid Derivatives

29