Chapter 4: Amino Acids

Matching
A) uncharged
B) deprotonated
C) three
D) -amino group
E) two
F) C-terminus
G) lysine
H) racemic mixture
I) zero
J) protonated
K) isoleucine
L) tryptophan
M) phenylalanine

1. When a peptide bond is formed, an ______ reacts with a carboxylate group.

Ans: D

Section: 4.1.B
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

2. In the peptide Trp-Ser-Val, valine is at the ______.

Ans: F

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

3. At a pH above its pK, the phenolic group of tyrosine is ______.

Ans: B

Section: 4.1.C
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
4. At a pH below its pK, the -amino group of lysine is ______.
Ans: J

Section: 4.1.D
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

5. At a pH below its pK, the -carboxylate group of Asp is ______.

Ans: A or J

Section: 4.1.D
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

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

Ans: I

Section: 4.1.A
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

7. Biological systems usually produce a single enantiomer, whereas chemical synthesis produces
a ______.
Ans: H

Section: 4.2
Level of Difficulty: Easy
Learning objective: Amino Acid Structure

8. In the tripeptide Trp-Val-Phe, the N-terminal residue is ______.

Ans: L

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

9. In the tripeptide Lys-Pro-Ile, the C-terminal residue is _________.

Ans: K

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

10. In the tripeptide Lys-Pro-Ile, there are ______ charged groups at pH 7.

Ans: C

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

Multiple Choice

11. Which of the following amino acids has a charged polar side chain at pH 7?
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

12. 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

13. Which of the following amino acids has an uncharged polar side chain at pH 7?
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

14. At pH 7, arginine (pKs are -carboxylate 1.82, -amino 8.99, guanidino 12.48) would be
charged as follows:
A) 0 -carboxylate, 0 -amino, +1 guanidino, +1 net charge
B) +1 -carboxylate, 0 -amino, -1 guanidino, 0 net charge
C) +1 -carboxylate, -1 -amino, -1 guanidino, -1 net charge
D) -1 -carboxylate, +1 -amino, +1 guanidino, +1 net charge
E) -1 -carboxylate, 0 -amino, +1 guanidino, 0 net charge

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

15. At pH 7, aspartic acid (pKs are -carboxylate 1.99, -amino 9.9, -carboxylate 3.9 ) would be
charged as follows:
A) 0 -carboxylate, +1 -amino, 0 -carboxylate, +1 net charge
B) -1 -carboxylate, +1 -amino, -1 -carboxylate, -1 net charge
C) 0 -carboxylate, -1 -amino, 0 -carboxylate, -1 net charge
D) +1 -carboxylate, -1 -amino, +1 -carboxylate, +1 net charge
E) +1 -carboxylate, +1 -amino, +1 -carboxylate, +3 net charge

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

16. At pH 11, glutamic acid (pKs are -carboxylate 2.1, -amino 9.47, -carboxylate 4.07. would
be charged as follows:
A) +1 -carboxylate, 0 -amino, +1 -carboxylate, +2 net charge
B) -1 -carboxylate, +1 -amino, -1 -carboxylate, -1 net charge
C) 0 -carboxylate, 0 -amino, 0 -carboxylate, 0 net charge
D) +1 -carboxylate, -1 -amino, +1 -carboxylate, +1 net charge
E) -1 -carboxylate, 0 -amino, -1 -carboxylate, -2 net charge

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

17. At pH 4, histidine (pKs are -carboxylate 1.8, -amino 9.33, 6.04 imidazole) would be
charged as follows:
A) +1 -carboxylate, 0 -amino, -1 imidazole, 0 net charge
B) -1 -carboxylate, +1 -amino, 0 imidazole, 0 net charge
C) +1 -carboxylate, +1 -amino, -1 imidazole, +1 net charge
D) -1 -carboxylate, +1 -amino, +1 imidazole, +1 net charge
E) 0 -carboxylate, + -amino, +1 imidazole, +2 net charge

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

18. At pH 5, cysteine (pKs are -carboxylate 1.92, -amino 10.7, sulfhydryl 8.37 ) would be
charged as follows:
A) 0 -carboxylate, 0 -amino, 0 sulfhydryl, 0 net charge
B) +1 -carboxylate, -1 -amino, -1 sulfhydryl, -1 net charge
C) -1 -carboxylate, +1 -amino, +1 sulfhydryl, +1 net charge
D) -1 -carboxylate, +1 -amino, 0 sulfhydryl, 0 net charge
E) +1 -carboxylate, -1 -amino, 0 sulfhydryl, 0 net charge

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

19. At pH 1, lysine (pKs are -carboxylate 2.16, -amino 9.06, -amino 10.54 ) would be charged
as follows:
A) 0 -carboxylate, -1 -amino, -1 -amino, -2 net charge
B) -1 -carboxylate, +1 -amino, +1 -amino, +1 net charge
C) +1 -carboxylate, +2 -amino, +2 -amino, +5 net charge
D) 0 -carboxylate, +1 -amino, +1 -amino, +2 net charge
E) +2 -carboxylate, +1 -amino, +1 -amino, +4 net charge

Ans: D
Section: 4.1.C
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure
20. The disulfide bond between two cysteine molecules:
A) is a peptide bond.
B) is an ionic bond 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 weak ion-induced dipole attraction.

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

21. What proportion of the 20 amino acids are 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 Easy:
Learning objective: Amino Acid Structure

22. Which of the following statements is/are true?

A) amino acids can be derived from purines and pyrimidines
B) purines and pyrimidines can be derived from amino acids
C) no protein contains every standard amino acid
D) A and C
E) B and C

Ans: B
Section: 4.1
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
23. The isoelectronic point of an amino acid is the point where:
A) The pK of the carboxylic acid is the same as the amino group
B) Sodium ions are attracted to the amino groups
C) the solubility of the amino acid is maximized
D) the amino acid racemizes
E) the amino acid carries no net electrical charge

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

24. Amino acid side-chain residues have:

A) a positive charge in every situation
B) pKs that assure the solubility of every protein
C) constant pKs no matter what aqueous environment they are found in
D) different pKs 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

25. 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 on protein hydrolysis

Ans: D
Section: 4.1.E
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
26. The formation of a dipeptide from two amino acids requires:
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

27. 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

28. 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
29. What is the abbreviation for the peptide valylarginylisoleucine?
A) Val-Arg-Ile
B) Val-Agn-Leu
C) Vln-Arg-Ile
D) Val-Agn-Isl
E) Vln-Arg-Leu

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

30. The least abundant amino acid in proteins is:

A) V
B) W
C) G
D) F
E) A

Ans: B
Section: 4.1
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

31. Zwitterions are:

A) amino acids
B) ionic molecules that are racemic
C) molecules 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
32. 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: Amino Acid Structure

33. The __________ character of most standard amino acids causes solutions of amino acids to
rotate plane polarized light.
A) chiral
B) zwitterionic
C) polar
D) all of the above
E) none of the above

Ans: A
Section: 4.2
Level of Difficulty: easy
Learning objective: Amino Acid Structure

34. All amino acids derived from proteins have the same conformation as:
A) L-glyceraldehyde
B) dextro-glyceraldehyde
C) D-glucose
D) cis-lysine
E) glycine

Ans: A
Section: 4.2
Level of Difficulty: Easy
Learning objective: Amino Acid Structure
35. Typically, ‘unnatural’ amino acids with side chain modifications
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 synthesis
D) are toxic
E) are racemic

Ans: C
Section: 4.3.A
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure

36. An amide bond between a side-chain carboxylate and an -amino group is also called a(n):
A) disulfide bond
B) amino amide bond
C) nor-peptide bond
D) isopeptide bond
E) hormone bond

Ans: D
Section: 4.3
Level of Difficulty: Moderate
Learning objective: Amino Acid Structure