Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 27, Problem 27.1P
Interpretation Introduction

(a)

Interpretation:

The structure of tryptophylglycylisoleucylaspartic acid is to be predicted.

Concept introduction:

The chemical compounds in which carbon is bonded with the acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three-word abbreviation or one-word abbreviation is used for amino acids.

Expert Solution
Check Mark

Answer to Problem 27.1P

The structure of tryptophylglycylisoleucylaspartic acid is shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  1

Explanation of Solution

The name of the peptide is triptophylglycylisoleucylaspartic acid.

This peptide is made up of four amino acids which are linked by peptide bonds. The amino acids are tryptophan, glycine, isoleucine, and aspartic acid.

The structures of triptophane, glycine, isoleucine, and aspartic acid are shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  2

Figure 1

Therefore, the structure of tryptophylglycylisoleucylaspartic acid is shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  3

Figure 2

Conclusion

The structure of tryptophylglycylisoleucylaspartic acid is shown in Figure 2.

Interpretation Introduction

(b)

Interpretation:

The structure of Glu-Gln-Phe-Arg is to be predicted.

Concept introduction:

The chemical compounds in which carbon is bonded with the acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three-word abbreviation or one-word abbreviation is used for amino acids.

Expert Solution
Check Mark

Answer to Problem 27.1P

The structure of Glu-Gln-Phe-Arg is shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  4

Explanation of Solution

The name of the peptide is Glu-Gln-Phe-Arg.

This peptide is made up of four amino acids which are linked by peptide bonds. The amino acids are glutamic acid, glutamine, phenylalanine, and arginine.

The structures of glutamic acid, glutamine, phenylalanine, and arginine are shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  5

Figure 3

Therefore, the structure of Glu-Gln-Phe-Arg is shown below.

Organic Chemistry, Chapter 27, Problem 27.1P , additional homework tip  6

Figure 4

Conclusion

The structure of Glu-Gln-Phe-Arg is shown in Figure 4.

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Students have asked these similar questions
Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.
Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin, appeared in Section 22.6B.)
Answer the (b) part of the question 6  (a) A decapeptide has the following amino acid composition: Ala2 , Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val Partial hydrolysis yields the following tripeptides: Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala+ Lys-Val-Phe + Val-Phe-Gly. Reaction of the decapeptide with 2,4-dinitrofluorobenzene yields 2,4-dinitrophenylysine. From the experimental data, deduce the primary structure of the decapeptide. (b) Suggest a scheme you will follow to synthesize the dipeptide Ala-Gly

Chapter 27 Solutions

Organic Chemistry

Ch. 27 - Prob. 27.12PCh. 27 - Prob. 27.13PCh. 27 - Prob. 27.14PCh. 27 - Prob. 27.15PCh. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Prob. 27.25PCh. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - Prob. 27.43APCh. 27 - Prob. 27.44APCh. 27 - Prob. 27.45APCh. 27 - Prob. 27.46APCh. 27 - Prob. 27.47APCh. 27 - Prob. 27.48APCh. 27 - Prob. 27.49APCh. 27 - Prob. 27.50APCh. 27 - Prob. 27.51APCh. 27 - Prob. 27.52APCh. 27 - Prob. 27.53APCh. 27 - Prob. 27.54APCh. 27 - Prob. 27.55APCh. 27 - Prob. 27.56APCh. 27 - Prob. 27.57APCh. 27 - Prob. 27.58APCh. 27 - Prob. 27.59APCh. 27 - Prob. 27.60APCh. 27 - Prob. 27.61APCh. 27 - Prob. 27.62APCh. 27 - Prob. 27.63APCh. 27 - Prob. 27.64APCh. 27 - Prob. 27.65APCh. 27 - Prob. 27.66APCh. 27 - Prob. 27.67APCh. 27 - Prob. 27.68APCh. 27 - Prob. 27.69APCh. 27 - Prob. 27.70APCh. 27 - Prob. 27.71APCh. 27 - Prob. 27.72APCh. 27 - Prob. 27.73APCh. 27 - Prob. 27.74APCh. 27 - Prob. 27.75APCh. 27 - Prob. 27.76APCh. 27 - Prob. 27.77APCh. 27 - Prob. 27.78APCh. 27 - Prob. 27.79APCh. 27 - Prob. 27.80APCh. 27 - Prob. 27.81APCh. 27 - Prob. 27.82APCh. 27 - Prob. 27.83AP
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