AMINO ACIDS, PEPTIDES, AND PROTEINS

MULTIPLE-CHOICE QUESTIONS
1. Which amino acid would have its isoelectric point near pH = 10?

A) I B) II C) III D) IV E) V

2. Which amino acid would have its isoelectric point near pH = 3?

A) I B) II C) III D) IV E) V

3. Which amino acid would have its isoelectric point near pH = 10?

A) I B) II C) III D) IV E) V

4. Which amino acid would have its isoelectric point near pH = 10?
A) Glycine B) Tryptophan C) Serine D) Proline E) Lysine

5. Which amino acid would have its isoelectric point near pH range 5-7?
A) Leucine B) Threonine C) Methionine D) Arginine E) Cystine

6. Which amino acid would have its isoelectric point near pH range 5-7?
A) Glycine
B) Proline
C) Cysteine
D) Glutamine
E) All of these amino acids have isoelectric point in the pH range 5-7

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International University, Vietnam National University – HCMC
7. What might be concluded upon determining that an unknown amino acid has its isoelectric point near
pH = 10?
A) It must have a hydrophobic side chain
B) It must have a hydrophilic side chain
C) Its side chain must contain a basic group
D) Its side chain must contain an acidic group
E) None of the above is a valid conclusion

8. What might be concluded upon determining that an unknown amino acid has its isoelectric point near
pH = 3?
A) It must have a hydrophobic side chain
B) It must have a hydrophilic side chain
C) Its side chain must contain a basic group
D) Its side chain must contain an acidic group
E) None of the above is a valid conclusion

9. The pH at which the concentration of the dipolar ion (zwitterion) form of an amino acid is at a
maximum and the cationic and anionic forms are at equal concentrations is termed the
A) end point.
B) equivalence point.
C) neutral point.
D) isoelectric point.
E) dipolar point.

10. What is the pI of the following amino acid?

A) 1.6 B) 3.2 C) 5.5 D) 6.2 E) 7.0

11. What is the pI of the following amino acid?

A) 2.1 B) 3.2 C) 5.9 D) 6.5 E) 7.0

12. What is the pI of the following amino acid?

A) 1.5 B) 6.3 C) 5.6 D) 9.8 E) 6.8

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International University, Vietnam National University – HCMC
13. What is the pI of the following amino acid?

A) 12 B) 3.6 C) 4.8 D) 6.0 E) 7.2

14. Consider the following tripeptide:

What is the best estimate of the pI of this compound?

A) 6.2 B) 7.1 C) 9.2 D) 10.1 E) 11.3

15. Which amino acid would have its isoelectric point near pH = 14?

A) I B) II C) III D) IV E) V

16. The predominant form of aspartic acid in water at pH = 1 would be:

A) I B) II C) III D) IV E) V

17. For the accompanying fully-protonated amino acid, what is the arrangement of pKa values in order of
increasing magnitude?

A) I < II < III B) II < I < III C) III < I < II D) III < II < I E) II < III < I

18. Which of these amino acids contains a hydrophobic side chain?

A) Lysine
B) Serine
C) Methionine

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International University, Vietnam National University – HCMC
D) Arginine
E) Cysteine

19. Which of these natural amino acids contains an amide function?

A) Asparagine
B) Proline
C) Arginine
D) Histidine
E) None of these

20. Which of these natural amino acids contains a heterocyclic ring?

A) Asparagine
B) Proline
C) Arginine
D) Histidine
E) Two of these

21. Which of these natural amino acids contains an amide function?

A) Asparagine
B) Methionine
C) Cysteine
D) Glutamine
E) Two of these

22. Which of these natural amino acids contains two carboxylic acid groups?
A) Cystine
B) Cysteine
C) Glutamic acid
D) A and B
E) A and C

23. Which of these natural amino acids contains a phenolic group?

A) Phenylalanine
B) Tyrosine
C) Tryptophan
D) 4-Hydroxyproline
E) Serine

24. Which of these natural amino acids contains a pyrrolidine ring?

A) Phenylalanine
B) Tyrosine
C) Tryptophan
D) 4-Hydroxyproline
E) Serine

25. Which of these natural amino acids contains an indole ring?

A) Phenylalanine
B) Tyrosine
C) Tryptophan
D) 4-Hydroxyproline
E) Asparigine

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International University, Vietnam National University – HCMC
26. Which of these natural amino acids contains an imidazole ring?
A) Histidine
B) Lysine
C) Tryptophan
D) 4-Hydroxyproline
E) Two of the above
27. Which of these natural amino acids contains an –OH group?
A) Serine
B) Threonine
C) Tyrosine
D) Two of these
E) All of these

28. Which of these natural amino acids, when present in a polypeptide, is likely to exhibit significant
hydrogen bonding through its side chain?
A) Serine
B) Threonine
C) Tyrosine
D) Two of these
E) All of these

29. Which of these natural amino acids, when present in a polypeptide, is not likely to exhibit significant
hydrogen bonding through its side chain?
A) Leucine
B) Threonine
C) Tyrosine
D) Serine
E) All of these are likely to exhibit significant hydrogen bonding through the side chain

30. Which amino acid is least likely to be found in a natural protein?

A) I B) II C) III D) IV E) V

31. Which amino acid is unlikely to be found in a natural protein?

A) I B) II C) III D) IV E) V

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International University, Vietnam National University – HCMC
32. Which of these amino acids is formed from a precursor amino acid only after the latter has been
incorporated into a polypeptide chain?
A) Serine
B) Arginine
C) Isoleucine
D) Tryptophan
E) Hydroxyproline

33. Which of these amino acids is described as an “essential” amino acid?

A) Methionine
B) Phenylalanine
C) Isoleucine
D) Tryptophan
E) All of these are “essential” amino acids

35. Pipecolic acid logically would be substituted for which natural amino acid in the synthesis of peptide
analogs?

A) Histidine
B) Proline
C) Tryptophan
D) Phenylalanine
E) Tyrosine

36. Logically, the following “unnatural” amino acid would be substituted for which natural amino acid in
the synthesis of peptide analogs?

A) Tyrosine
B) Proline
C) Tryptophan
D) Phenylalanine
E) Tyrosine

37. Logically, the following “unnatural” amino acid would be substituted for which natural amino acid in
the synthesis of peptide analogs?

A) Methionine
B) Cysteine
C) Cystine
D) Tyrosine
E) It could be substituted for all of these amino acids

38. Logically, the following “unnatural” amino acid would be substituted for which natural amino acid in
the synthesis of peptide analogs?

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International University, Vietnam National University – HCMC
A) Aspartic acid
B) Glutamine
C) Lysine
D) Asparagine
E) Glutamic acid

39. Logically, the following “unnatural” amino acid would be substituted for which natural amino acid in
the synthesis of peptide analogs?

A) Leucine
B) Lysine
C) Arginine
D) Alanine
E) Valine

40. Which of the following would provide a synthesis of alanine?

A) CH2=CHCH2OH, HBr, CrO3/H2SO4/H2O; then xs NH3
B) Potassium phthalimide, ClCH2CO2C2H5; then KOH/H2O; then HCl
C) Potassium phthalimide, C6H5CH2Br; then KOH/H2O; then CO2, H3O+
D) CH3CH2COOH, (C6H5)3CNa; then NH3
E) Answers A) and B)

41. Which of the following would provide a synthesis of valine?

A) (CH3)2C=CHCH2OH, HBr/peroxides; CrO3/H2SO4/H2O; then xs NH3
B) Potassium phthalimide, (CH3)2CHCHClCO2C2H5; then KOH/H2O; then HCl
C) Potassium phthalimide, (CH3)2CHCH2Br; then KOH/H2O; then CO2, H3O+
D) CH3CH2COOH, (C6H5)3CNa; then NH3
E) Answers A) and B)

42. Which of the following would provide a synthesis of leucine?

A) (CH3)2C=CHCH2OH, HBr/peroxides; CrO3/H2SO4/H2O; then xs NH3
B) Potassium phthalimide, BrCH(CO2C2H5)2; (CH3)2CHCHClCO2C2H5; then KOH/H2O; then HCl
(85%), heat
C) Potassium phthalimide, BrCH(CO2C2H5)2; (CH3)2CHCH2Br; then KOH/H2O; then HCl (85%), heat
D) (CH3)2CHCOOH, PCl5; then NH3
E) Answers A) and C)

43. Which of the following would provide a synthesis of phenylalanine?

A) Phenylacetaldehyde, NH3, HCN; H3O+, heat
B) Potassium phthalimide, BrCH(CO2C2H5)2; C6H5CH2Br; then KOH/H2O; then HCl (85%), heat
C) Potassium phthalimide, (C6H5)CH2CH2Br; then KOH/H2O; then HCl (85%), heat
D) C6H5CH2COOH, SOCl2; then NH3
E) Answers A) and B)

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International University, Vietnam National University – HCMC
44. What product(s) would you expect from the following reaction?

A) I B) II C) III D) IV E) V

45. Which is an isolable intermediate in the Strecker synthesis of an amino acid?

A) I B) II C) III D) IV E) V

46. The primary structure of a protein refers to its:

A) sequence of amino acid residues.
B) disulfide bonds.
C) helical structure.
D) hydrogen bonding.
E) All of these

47. The secondary structure of proteins is derived from:

A) peptide linkages.
B) disulfide linkages.
C) hydrogen bond formation.
D) hydrophobic interactions.
E) acid-base interactions.

48. Which attractive force is responsible for maintaining the tertiary structure of a protein?
A) Disulfide linkages
B) Hydrogen bonds
C) van der Waals forces
D) Hydrophobic interactions
E) All of these

49. Disulfide bonds in proteins:

A) result from an oxidation of thiols.
B) help to maintain the shape of proteins.
C) can be broken by reduction.

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International University, Vietnam National University – HCMC
D) can link two cysteine amino acid residues.
E) All of these above

50. Which of these amino acid residues is expected to prefer the interior of a protein to the exterior when
the protein is in aqueous medium?
A) Threonine B) Valine C) Serine D) Aspartic acid E) Lysine

51. A "conjugated protein" is one which:

A) possesses catalytic properties.
B) is a digestive enzyme.
C) exists largely as an a -helix.
D) contains unsaturated amino acids.
E) contains a nonprotein group as part of the molecule.

52. A pentapeptide has the molecular formula: Asp, Glu, His, Phe, Val. Partial hydrolysis of the
pentapeptide gives: Val·Asp, Glu·His, Phe·Val, and Asp·Glu. What is the amino acid sequence of the
pentapeptide?
A) Phe· V al· Asp· Glu· His
B) His· Glu· Asp· V al· Phe
C) Asp· Glu· His· Phe· V al
D) Phe· V al· Glu· His· Asp
E) Glu· His· Phe· V al· Asp

53. A heptapeptide Ala2, Glu, Phe, Pro, Tyr, Val gives labeled alanine when heated with DNFB followed
by hydrolysis. On partial hydrolysis the unlabeled heptapeptide gives the following: Ala·Glu, Pro·Tyr,
Ala·Val, Tyr·Ala, Val·Phe·Pro. What is the amino acid sequence of the heptapeptide?
A) Ala·Phe·Pro·Tyr·Ala·Glu·Val
B) Ala·Val·Phe·Pro·Tyr·Ala·Glu
C) Ala·Val·Phe·Pro·Tyr·Glu·Ala
D) Ala·Val·Phe·Tyr·Pro·Ala·Glu
E) Val·Ala·Phe·Tyr·Pro·Ala·Glu

54. How many different tripeptides can exist, each containing one residue of glycine, one of L-threonine,
and one of L-arginine?
A) 2 B) 3 C) 6 D) 8 E) 9

55. Which of these amino acids has the R configuration at the stereogenic center but, nonetheless, is an L
amino acid?

A) I B) II C) III D) IV E) V

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International University, Vietnam National University – HCMC
56. Which of these amino acids cannot be described as an L amino acid?

A) I B) II, IV and V C) I and III D) II and IV E) III and V

57. Which of these amino acids is a D amino acid?

A) I B) II C) III D) IV E) V

58. Which of these amino acids is an R amino acid?

A) II and IV B) IV and V C) I and III D) V E) All of these are

R amino acids

59. Which of the following amino acids is theoretically capable of existing in diastereomeric forms?

A) I B) II C) III D) IV E) V

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International University, Vietnam National University – HCMC
60. Which amino acid is achiral?

A) I B) II C) III D) IV E) V

SHORT ANSWER QUESTIONS

61. The exact sequence of the different a -amino acids along the protein chain is called the
________________ of the protein.

62. The Henderson-Hasselbach equation shows that the ________________ of an acid is the
________________ at which the acid is half-neutralized.

63. The folding of the polyamide chain gives rise to higher levels of complexity called the
_______________ and ______________ of the protein.

64. The 22 a -amino acids can be subdivided into three different types on the basis of the structures of
their side chains. These three types are: ____________.

65. The pH at which the concentration of the zwitterionic form (dipolar form) of an amino acid is at its
highest and the concentrations of the cationic and anionic forms are equal is called the _____________.

66. One common method of analysis used to measure the approximate molecular weight of a protein is
called _____________.

67. Draw structures to represent what happens when valine is dissolved in a strongly acidic solution
(pH=0).

68. Draw structures to represent what happens when valine is dissolved in a strongly basic solution
(pH=14).

69. Draw structures to represent what happens when lysine is dissolved in a strongly acidic solution
(pH=0).

70. Draw structures to represent what happens when lysine is dissolved in a strongly basic solution
(pH=14).

----------The End----------

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International University, Vietnam National University – HCMC