Textbook Question
Show the steps in the synthesis of the tetrapeptide in Problem 34, using Merrifield's method.
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Ch. 21 - Amino Acids, Peptides, and Proteins
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 22, Problem 35
a. Calculate the overall yield of bradykinin when the yield for the addition of each amino acid to the chain is 70%.
b. What would be the overall yield of a peptide containing 15 amino acids if the yield for the incorporation of each is 80%
Verified step by step guidance1
Step 1: Understand the problem. The overall yield of a peptide synthesis is calculated by multiplying the yield of each step (amino acid addition) for the total number of steps. This is because each step has a probability of success, and the overall yield is the product of these probabilities.
Step 2: For part (a), identify the number of amino acids in bradykinin. Bradykinin is a peptide composed of 9 amino acids. The yield for each step is given as 70%, which can be expressed as 0.70 in decimal form.
Step 3: Use the formula for overall yield: \( \text{Overall Yield} = (\text{Yield per step})^{\text{Number of steps}} \). Substitute the values for bradykinin: \( \text{Overall Yield} = (0.70)^9 \).
Step 4: For part (b), identify the number of amino acids in the peptide, which is 15. The yield for each step is given as 80%, or 0.80 in decimal form. Use the same formula: \( \text{Overall Yield} = (\text{Yield per step})^{\text{Number of steps}} \). Substitute the values: \( \text{Overall Yield} = (0.80)^{15} \).
Step 5: To complete the problem, calculate the numerical values for both parts (a) and (b) using the formulas provided. This will give the overall yield for bradykinin and the 15-amino-acid peptide.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Peptide Synthesis Yield
In peptide synthesis, the yield refers to the efficiency of incorporating each amino acid into the growing peptide chain. It is typically expressed as a percentage, indicating the fraction of successful reactions compared to the total number of attempts. Understanding yield is crucial for predicting the final amount of peptide produced after multiple coupling reactions.
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Merrifield Solid-Phase Peptide Synthesis Concept 1
Multiplicative Yield Calculation
When calculating the overall yield of a multi-step synthesis process, the yields of each step are multiplied together. This is because each step's yield affects the subsequent steps; if one step has a lower yield, it reduces the amount of product available for the next step. This concept is essential for determining the final yield of complex molecules like peptides.
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04:37Draw all of the monochlorination products and calculate percentage yields.
Bradykinin Structure
Bradykinin is a peptide composed of a specific sequence of amino acids, typically consisting of nine residues. Understanding its structure is important for calculating yields, as each amino acid addition contributes to the final sequence. The specific sequence and the number of amino acids directly influence the overall yield calculations in peptide synthesis.
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03:04Drawing Resonance Structures
Related Practice
Textbook Question
Show the steps in the synthesis of the tetrapeptide Leu-Phe-Ala-Val.
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Textbook Question
What is the configuration about each of the asymmetric centers in aspartame?
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Textbook Question
What dipeptides would be formed by heating a mixture of valine and N-protected leucine?
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Textbook Question
A decapeptide undergoes partial hydrolysis to give peptides whose amino acid compositions are shown. Reaction of the intact decapeptide with Edman's reagent releases PTH-Gly. What is the sequence of the decapeptide?
1. Ala, Trp
2. Val, Pro, Asp
3. Pro, Val
4. Ala, Glu
5. Trp, Ala, Arg
6. Arg, Gly
7. Glu, Ala, Leu
8. Met, Pro, Leu, Glu
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Textbook Question
Write the mechanism for the reaction of a cysteine side chain with iodoacetic acid.
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