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Ch 4 - Problems

Ch 4 - Problems

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Published by Khris Griffis

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Published by: Khris Griffis on Apr 17, 2010
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11/29/2013

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1.
Identify the amino acids that differ from each other by a single methyl or methylene group.
Answer:
Gly and Ala; Ser and Thr; Val, Leu, and Ile; Asn and Gln; Asp and Glu.
2.
The 20 standard amino acids are called
α
-amino acids. Certain
β
-amino acids are found in nature. Drawthe structure of 
β
-alanine (3-amino-
n
-propionate).
Answer:
+
H
3
 N—CH
2
 —CH
2
 —COO
 – 
3.
Identify the hydrogen bond donor and acceptor groups in asparagine.
Answer:
Hydrogen bond donors:
α
-amino group, amide nitrogen. Hydrogen bond acceptors:
α
-carboxylate group,amide carbonyl.
4.
Draw the dipeptide Asp-His at pH 7.0.
Answer:5.
Calculate the number of possible pentapeptides that contain one residue each of Ala, Gly, His, Lys, andVal.
Answer:
The first residue can be one of five residues, the second one of the remaining four, etc.
6.
Determine the net charge of the predominant form of Asp at (a) pH 1.0, (b) pH 3.0, (c) pH 6.0, and (d) pH11.0.
Answer:(a)
+1;
(b)
0;
(c)
 –1;
(d)
 –2.
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c04/dm9ld...1 of 54/17/2010 9:07 AM
 
7.
Calculate the p
 I 
of (a) Ala, (b) His, and (c) Glu.
Answer:(a)
 p
 I 
= (2.35 + 9.87)/2 = 6.11
(b)
 p
 I 
= (6.04 + 9.33)/2 = 7.68
(c)
 p
 I 
= (2.10 + 4.07)/2 = 3.08
8.
A sample of the amino acid tyrosine is barely soluble in water. Would a polypeptide containing only Tyr residues, poly(Tyr), be more or less soluble, assuming the total number of Tyr groups remains constant?
Answer:
The polypeptide would be even less soluble than free Tyr, because most of the amino and carboxylategroups that interact with water and make Tyr at least slightly soluble are lost in forming the peptide bondsin poly(Tyr).
9.
Circle the chiral carbons in the following compounds:
Answer:10.
Draw the four stereoisomers of threonine.
Answer:
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c04/dm9ld...2 of 54/17/2010 9:07 AM
 
11.
The two C
α
H atoms of Gly are said to be prochiral, because when one of them is replaced by another group, C
α
becomes chiral. Draw a Fischer projection of Gly and indicate which H must be replaced withCH
3
to yield
D
-Ala.
Answer:12.
The bacterially produced antibiotic gramicidin A forms channels in cell membranes that allow the freediffusion of Na
+
and K 
+
ions, thereby killing the cell. This peptide consists of a sequence of 
D
- and
L
-amino acids. The sequence of a segment of five amino acids in gramicidin A is R–Gly– 
L
-Ala– 
D
-Leu– 
L
-Ala– 
D
-Val–R 
. Complete the Fischer projection below by adding the correct group to each vertical bond.
Answer:13.
Describe isoleucine (as shown in Table 4-1) using the
 RS
system.
Answer:
(2
S
,3
S
)-Isoleucine
14.
Some amino acids are synthesized by replacing the keto group (CO) of an organic acid known as an
α
-keto acid with an amino group . Identify the amino acids that can be produced this way
Problemshttp://edugen.wiley.com/edugen/courses/crs1900/rc/voet9301c04/dm9ld...3 of 54/17/2010 9:07 AM

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