Chapter 4: Amino Acids

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

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

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

Ans: D
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
2. In the peptide Trp-Ser-Val, valine is at the ______.
Ans: F
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
3. At a pH above its pK, the phenolic group of tyrosine is ______.
Ans: B
Section: 4.1 The Amino Acids of Proteins
Level of Difficulty: Easy
4. At a pH below its pK, the -amino group of lysine is ______.
Ans: J

Section: 4.1. The Amino Acids of Proteins

Level of Difficulty: Easy
5. At a pH below its pK, the -carboxylate group of Asp is ______.
Ans: A or J
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
6. The net charge of the zwitterion form of Gly is ______.
Ans: I
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
7. Biological systems usually produce a single enantiomer, whereas chemical synthesis produces
a ______.
Ans: H
Section: 4.2. Optical Activity
Level of Difficulty: Easy
8. In the tripeptide Trp-Val-Phe, the N-terminal residue is ______.
Ans: L
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
9. In the tripeptide Lys-Pro-Ile, the C-terminal residue is _________.
Ans: K
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy
10. In the tripeptide Lys-Pro-Ile, there are ______ charged groups at pH 7.
Ans: C
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Easy

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. The Amino Acids of Proteins
Level of Difficulty: Easy
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. The Amino Acids of Proteins
Level of Difficulty: Easy
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. The Amino Acids of Proteins
Level of Difficulty: Easy
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.The Amino Acids of Proteins
Level of Difficulty: Moderate
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. The Amino Acids of Proteins
Level of Difficulty: Moderate
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. The Amino Acids of Proteins
Level of Difficulty: Moderate
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. The Amino Acids of Proteins

Level of Difficulty: Moderate

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. The Amino Acids of Proteins
Level of Difficulty: Moderate
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. The Amino Acids of Proteins
Level of Difficulty: Moderate
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. The Amino Acids of Proteins
Level of Difficulty: Easy

21. 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. The Amino Acids of Proteins
Level of Difficulty: Easy

22. 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. The Amino Acids of Proteins
Level of Difficulty: Moderate
23. 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. The Amino Acids of Proteins
Level of Difficulty: Moderate

24. 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. The Amino Acids of Proteins
Level of Difficulty: Easy

25. 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. The Amino Acids of Proteins
Level of Difficulty: Easy
26. 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. The Amino Acids of Proteins
Level of Difficulty: Easy

27. 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. The Amino Acids of Proteins
Level of Difficulty: Moderate

28. 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. The Amino Acids of Proteins
Level of Difficulty: Easy

29. The least abundant amino acid in proteins is:

A) V
B) W
C) G
D) F
E) A
Ans: B
Section: 4.1. The Amino Acids of Proteins
Level of Difficulty: Moderate

30. 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. The Amino Acids of Proteins
Level of Difficulty: Easy

31. All the standard amino acids except ____ are optically active.
A) Pro
B) Arg
C) Trp
D) Gly
E) Phe
Ans: D
Section: 4.2. Optical Activity
Level of Difficulty: Easy
32. 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. Optical Activity
Level of Difficulty: easy

33. 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. Optical Activity
Level of Difficulty: Easy
34. 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. Nonstandard Amino Acids
Level of Difficulty: Moderate