General, Organic, and Biological Chemistry - 4th edition
General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Chapter 21, Problem 56P

Decide if the side chains of the amino acid residues in the following peptides are nonpolar or polar, and label the hydrophobic and hydrophilic end of each peptide.

  1. VLLFGEDEK
  2. RKVSFLGAA

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation:

The polarity of the side chains of the amino acid residue in the given peptide should be determined and also label the hydrophilic and hydrophobic ends of the given peptide.

VLLFGEDEK

Concept Introduction:

Amino acids are organic compounds containing two functional groups namely amino and carboxylic group. Amino group is attached to the alpha carbon, carbon adjacent to the carbonyl group making them alpha amino acids.

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  1

This table gives information about the polarity of the side chains:

Name of Amino AcidOne-letter abbreviationStructureSide chain PolaritySide chain
AlanineAGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  2NonpolarHydrophobic
AsparagineNGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  3PolarHydrophilic
CysteineCGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  4NonpolarHydrophobic
GlutamineQGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  5PolarHydrophilic
GlycineGGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  6NonpolarHydrophobic
IsoleucineIGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  7NonpolarHydrophobic
LeucineLGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  8NonpolarHydrophobic
MethionineMGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  9NonpolarHydrophobic
PhenylalanineFGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  10NonpolarHydrophobic
ProlinePGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  11NonpolarHydrophobic
SerineSGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  12PolarHydrophilic
ThreonineTGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  13PolarHydrophilic
TryptophanWGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  14NonpolarHydrophobic
TyrosineYGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  15PolarHydrophilic
ValineVGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  16NonpolarHydrophobic
Aspartic acidDGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  17PolarHydrophilic
Glutamic acidEGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  18PolarHydrophilic
ArginineRGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  19PolarHydrophilic
HistidineHGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  20PolarHydrophilic
LysineKGeneral, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  21PolarHydrophilic

Answer to Problem 56P

The polarity of the side chains of amino acids are shown along with hydrophobic and hydrophilic end of the given peptide 'VLLFGEDEK' as follows:

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  22

Explanation of Solution

Side chains of amino acids are non-polar because only carbon and hydrogen atoms are present having very small dipole moment and tends to repel water. That's why non-polar amino acids are hydrophobic in nature.

Side chains of amino acids are polar because these proteins have those toms which are capable of forming hydrogen bonds have very high dipole moment and tends to attract water. That's why polar amino acids are hydrophilic in nature.

From the table, the sequence of peptide contains the following amino acids:

V = Valine is a non-polar amino acid.

L = Leucine is a non-polar amino acid.

F = Phenylalanine is a non-polar amino acid.

G = Glycine is a non-polar amino acid.

E = Glutamic acid is a polar amino acid.

D = Aspartic acid is a polar amino acid.

K = Lysine is a polar amino acid.

From the given peptide sequence 'VLLFGEDEK', Valine present at the right end and Lysine present at the left end of the sequence.

Valine is a non-polar amino acid and hydrophobic in nature.

Lysine is a non-polar amino acid and hydrophilic in nature.

Hydrophobic and hydrophilic ends along with polar and non-polar amino acids are indicated in the given sequence as follows:

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  23

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:

The polarity of the side chains of the amino acid residue in the given peptide should be determined and also label the hydrophilic and hydrophobic ends of the given peptide.

RKYSFLGAA

Concept Introduction:

Amino acids are organic compounds containing two functional groups namely amino and carboxylic group. Amino group is attached to the alpha carbon, carbon adjacent to the carbonyl group making them alpha amino acids.

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  24

Answer to Problem 56P

The polarity of the side chains of amino acids are shown along with hydrophobic and hydrophilic end of the given peptide 'RKYSFLGAA' as follows:

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  25

Explanation of Solution

Side chains of amino acids are non-polar because only carbon and hydrogen atoms are present having very small dipole moment and tends to repel water. That's why non-polar amino acids are hydrophobic in nature.

Side chains of amino acids are polar because these proteins have those toms which are capable of forming hydrogen bonds have very high dipole moment and tends to attract water. That's why polar amino acids are hydrophilic in nature.

From the table, the sequence of peptide 'RKYSFLGAA' contains the following amino acids:

R = Arginine is a polar amino acid.

K = Lysine is a polar amino acid.

Y = Tyrosine is a polar amino acid.

S = Serine acid is a polar amino acid.

F = Phenylalanine is a non-polar amino acid.

L = Leucine is a non-polar amino acid.

G = Glycine is a non-polar amino acid.

A = Alanine is a non-polar amino acid.

From the given peptide sequence 'RKYSFLGAA', Arginine present at the right end and Alanine present at the left end of the sequence.

Arginine is a polar amino acid and hydrophilic in nature.

Alanine is a non-polar amino acid and hydrophobic in nature.

Hydrophobic and hydrophilic ends along with polar and non-polar amino acids are indicated in the given sequence as follows:

General, Organic, and Biological Chemistry - 4th edition, Chapter 21, Problem 56P , additional homework tip  26

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Chapter 21 Solutions

General, Organic, and Biological Chemistry - 4th edition

Ch. 21.4 - Prob. 21.6PPCh. 21.5 - Prob. 21.6PCh. 21.6 - Prob. 21.7PCh. 21.6 - Prob. 21.8PCh. 21.6 - Prob. 21.9PCh. 21.7 - Why is hemoglobin more water soluble than ...Ch. 21.8 - Prob. 21.7PPCh. 21.8 - Prob. 21.11PCh. 21.9 - Prob. 21.8PPCh. 21.9 - Prob. 21.12PCh. 21.9 - Prob. 21.9PPCh. 21.9 - Prob. 21.13PCh. 21.10 - Prob. 21.14PCh. 21.10 - Prob. 21.15PCh. 21.10 - Prob. 21.16PCh. 21.10 - Prob. 21.17PCh. 21.10 - The nerve gas sarin acts as a poison by covalently...Ch. 21.10 - Prob. 21.19PCh. 21.10 - Explain why the proteins involved in blood...Ch. 21 - The amino acid alanine is a solid at room...Ch. 21 - Why is phenylalanine water soluble but...Ch. 21 - Draw the structure of a naturally occurring amino...Ch. 21 - Draw the structure of a naturally occurring amino...Ch. 21 - For each amino acid: [1] draw the L enantiomer in...Ch. 21 - For each amino acid: [1] draw the L enantiomer in...Ch. 21 - Draw both enantiomers of each amino acid and label...Ch. 21 - Which of the following Fischer projections...Ch. 21 - For each amino acid: [1] give the name; [2] give...Ch. 21 - For each amino acid: [1] give the name; [2] give...Ch. 21 - (a) Identify the amino acid shown with all...Ch. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Draw the structure of the neutral, positively...Ch. 21 - Locate the peptide bond in the dipeptide shown in...Ch. 21 - Label the N-terminal and C-terminal amino acids in...Ch. 21 - Melittin, the principal toxin of bee venom,...Ch. 21 - Cobratoxin is a neurotoxin found in the venom of...Ch. 21 - (a) Draw the structure of the two possible...Ch. 21 - (a) Draw the structure of the two possible...Ch. 21 - For each tripeptide: [1] draw the structure of the...Ch. 21 - For each tripeptide: [1] draw the structure of the...Ch. 21 - Prob. 43PCh. 21 - For each tripeptide: [1] identify the amino acids...Ch. 21 - What amino acids are formed by hydrolysis of the...Ch. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - Draw the structures of the amino acids formed when...Ch. 21 - Prob. 49PCh. 21 - Prob. 50PCh. 21 - Prob. 51PCh. 21 - Trypsin is a digestive enzyme that hydrolyzes...Ch. 21 - What type of intermolecular forces exist between...Ch. 21 - What type of interaction occur at each of the...Ch. 21 - Which peptide in each pair contains amino acids...Ch. 21 - Decide if the side chains of the amino acid...Ch. 21 - Which type of protein structure is indicated in...Ch. 21 - Label each of the following diagrams as...Ch. 21 - Prob. 59PCh. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Prob. 62PCh. 21 - Compare - keratin and hemoglobin with regard to...Ch. 21 - Compare collagen and myoglobin with regard to each...Ch. 21 - Prob. 65PCh. 21 - Prob. 66PCh. 21 - Describe the function or biological activity of...Ch. 21 - Describe the function or biological activity of...Ch. 21 - Prob. 69PCh. 21 - Prob. 70PCh. 21 - What class of enzyme catalyzes each of the...Ch. 21 - What class of enzyme catalyzes each of the...Ch. 21 - Prob. 73PCh. 21 - Prob. 74PCh. 21 - Prob. 75PCh. 21 - What kind of reaction is catalyzed by each of the...Ch. 21 - Prob. 77PCh. 21 - How will each of the following changes affect the...Ch. 21 - Prob. 79PCh. 21 - Prob. 80PCh. 21 - Prob. 81PCh. 21 - Prob. 82PCh. 21 - Prob. 83PCh. 21 - Prob. 84PCh. 21 - Prob. 85PCh. 21 - Prob. 86PCh. 21 - Why must vegetarian diets be carefully balanced?Ch. 21 - Prob. 88PCh. 21 - Sometimes an incision is cauterized (burned) to...Ch. 21 - Why is insulin administered by injection instead...Ch. 21 - Prob. 91PCh. 21 - The silk produced by a silkworm is a protein with...Ch. 21 - Explain the difference in the mechanism of action...Ch. 21 - Prob. 94PCh. 21 - Prob. 95CPCh. 21 - Suggest a reason for the following observation....
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