Domanda del libro di testo
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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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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
Capitolo 21, Problema 39
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
Guida verificata passo dopo passo1
Step 1: Understand the problem. The decapeptide undergoes partial hydrolysis, breaking it into smaller peptide fragments. The amino acid compositions of these fragments are provided. Additionally, Edman degradation releases PTH-Gly, indicating that Glycine is the N-terminal amino acid of the intact decapeptide.
Step 2: Analyze the fragments. Each fragment represents a portion of the decapeptide. The goal is to determine how these fragments fit together to reconstruct the full sequence. Start by identifying overlaps in amino acid compositions between fragments.
Step 3: Use the information from Edman degradation. Since Glycine is the N-terminal amino acid, identify a fragment that starts with Glycine. Fragment 6 (Arg, Gly) is a candidate, suggesting that the sequence begins with Gly-Arg.
Step 4: Look for overlaps between fragments to build the sequence. For example, Fragment 6 (Arg, Gly) overlaps with Fragment 5 (Trp, Ala, Arg) because Arg is common. This suggests the sequence Gly-Arg-Trp-Ala. Continue this process, ensuring that each fragment fits logically with the next.
Step 5: Verify the sequence. Ensure that all fragments are accounted for and that the final sequence contains all 10 amino acids. The sequence should also match the information provided by Edman degradation and the amino acid compositions of the fragments.
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Peptide Structure
Peptides are short chains of amino acids linked by peptide bonds. The sequence of amino acids in a peptide determines its structure and function. Understanding the primary structure, which is the linear sequence of amino acids, is crucial for deducing the overall sequence of the decapeptide in the question.
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Percorso guidato
3:07
Peptides Concept 1
Edman's Degradation
Edman's degradation is a method used to determine the amino acid sequence of a peptide. In this process, Edman's reagent reacts with the amino terminal of the peptide, releasing a phenylthiohydantoin (PTH) derivative of the first amino acid. The information from the released PTH-Gly indicates that glycine is the first amino acid in the sequence, which is essential for solving the question.
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Percorso guidato
3:10Peptide Sequencing: Edman Degradation Concept 1
Partial Hydrolysis
Partial hydrolysis of a peptide involves breaking some peptide bonds, resulting in smaller peptides. The amino acid compositions provided in the question are the products of this hydrolysis. Analyzing these compositions helps in reconstructing the original decapeptide sequence by identifying which combinations of smaller peptides can yield the intact sequence.
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Percorso guidato
1:19Peptide Sequencing: Partial Hydrolysis Concept 1
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