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Write the mechanism for the reaction of an amino acid with di-tert-butyl dicarbonate.
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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 75c
Show how valine can be prepared by
c. a reductive amination.
Guida verificata passo dopo passo1
Identify the starting material: To prepare valine via reductive amination, you need to start with the corresponding α-keto acid, which is α-ketoisovaleric acid (3-methyl-2-oxobutanoic acid). This compound has the same carbon skeleton as valine but contains a keto group instead of an amino group.
Understand the reductive amination process: Reductive amination involves the reaction of a carbonyl compound (in this case, the keto group of α-ketoisovaleric acid) with ammonia (NH₃) or a primary/secondary amine, followed by reduction to form the corresponding amine.
React the α-keto acid with ammonia: Add ammonia (NH₃) to the α-ketoisovaleric acid. This step forms an imine intermediate (a compound with a C=N bond) through a condensation reaction where water is eliminated.
Reduce the imine intermediate: Use a reducing agent, such as sodium cyanoborohydride (NaBH₃CN) or hydrogen gas (H₂) with a metal catalyst (e.g., Pd/C), to reduce the imine to a primary amine. This step converts the imine into the amino group, resulting in valine.
Isolate and purify the product: After the reaction is complete, isolate valine by techniques such as crystallization or chromatography, and confirm its structure using spectroscopic methods like NMR or IR.
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Reductive Amination
Reductive amination is a chemical reaction that involves the conversion of a carbonyl compound, such as an aldehyde or ketone, into an amine. This process typically includes the formation of an imine or enamine intermediate, which is then reduced to yield the corresponding amine. In the case of valine, this reaction can be used to introduce the amino group onto a suitable precursor, such as a keto acid.
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07:12
Reductive Amination
Valine Structure and Properties
Valine is an essential branched-chain amino acid with the chemical structure C5H11NO2. It features a side chain that is isopropyl, making it hydrophobic and contributing to its role in protein structure and function. Understanding valine's structure is crucial for recognizing how it can be synthesized through reductive amination, as the correct functional groups must be present in the starting materials.
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Percorso guidato
1:19Polymers Structure and Properties Concept 1
Keto Acids in Amino Acid Synthesis
Keto acids are organic compounds that contain a ketone functional group and can serve as precursors in amino acid synthesis. In the context of valine preparation, a keto acid such as alpha-ketovalerate can be used as the starting material. The reductive amination process will involve the reaction of this keto acid with ammonia or an amine, followed by reduction to form valine.
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Percorso guidato
1:16Synthesis of Amino Acids: Strecker Synthesis Example 1
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