ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 29.36P

What is the predominant form of each of the following amino acids at pH = 1 ? What is the overall charge on the amino acid at this pH ? (a) threonine; (b) methionine; (c) aspartic acid; (d) arginine

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The predominant form of threonine at pH=1 and the overall charge on it at this pH is to be predicted.

Concept introduction: At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. The overall charge on an amino acid at isoelectric point is 0.

Answer to Problem 29.36P

The predominant form of threonine at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  1

The overall charge on it is +1.

Explanation of Solution

At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. However, when the pH of solution goes below isoelectric point, the amine group and carboxyl group exists as N+H3 and COOH, respectively.

The isoelectric point of threonine is 5.60. Therefore, the predominant form of threonine at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  2

Figure 1

The overall charge on threonine at pH=1 is +1.

Conclusion

The predominant form of threonine at pH=1 is shown in Figure 1 and the overall charge on it is +1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The predominant form of methionine at pH=1 and the overall charge on it at this pH is to be predicted.

Concept introduction: At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. The overall charge on an amino acid at isoelectric point is 0.

Answer to Problem 29.36P

The predominant form of methionine at pH=1 is

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  3

The overall charge on it is +1.

Explanation of Solution

At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. However, when the pH of solution goes below isoelectric point, the amine group and carboxyl group exists as N+H3 and COOH, respectively.

The isoelectric point of methionine is 5.74. Therefore, the predominant form of methionine at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  4

Figure 2

The overall charge on methionine at pH=1 is +1.

Conclusion

The predominant form of methionine at pH=1 is shown in Figure 2 and the overall charge on it is +1.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The predominant form of aspartic acid at pH=1 and the overall charge on it at this pH is to be predicted.

Concept introduction: At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. The overall charge on an amino acid at isoelectric point is 0.

Answer to Problem 29.36P

The predominant form of aspartic acid at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  5

The overall charge on it is +1.

Explanation of Solution

At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. However, when the pH of solution goes below isoelectric point, the amine group and carboxyl group exists as N+H3 and COOH, respectively.

The isoelectric point of aspartic acid is 2.98. Therefore, the predominant form of aspartic acid at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  6

Figure 3

The overall charge on aspartic acid at pH=1 is +1.

Conclusion

The predominant form of aspartic acid at pH=1 is shown in Figure 3 and the overall charge on it is +1.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The predominant form of arginine at pH=1 and the overall charge on it at this pH is to be predicted.

Concept introduction: At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. The overall charge on an amino acid at isoelectric point is 0.

Answer to Problem 29.36P

The predominant form of arginine at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  7

The overall charge on it is +3.

Explanation of Solution

At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as N+H3 and carboxyl groups as COO. However, when the pH of solution goes below isoelectric point, the amine group and carboxyl group exists as N+H3 and COOH, respectively.

The isoelectric point of arginine is 10.76. Therefore, the predominant form of arginine at pH=1 is,

ORGANIC CHEMISTRY, Chapter 29, Problem 29.36P , additional homework tip  8

Figure 4

The overall charge on arginine at pH=1 is +3.

Conclusion

The predominant form of arginine at pH=1 is shown in Figure 4 and the overall charge on it is +3.

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Chapter 29 Solutions

ORGANIC CHEMISTRY

Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13 What alkene is needed to synthesize...Ch. 29 - Problem 29.14 Draw the structure of each peptide....Ch. 29 - Problem 29.15 Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18 Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19 Draw the structure of the...Ch. 29 - Problem 29.20 Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr: a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY