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Ch. 24 - Amino Acids, Peptides, and Proteins
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 24 - Amino Acids, Peptides, and ProteinsProblem 12c
Chapter 24, Problem 12c

Show how you would use a Strecker synthesis to make
(c) aspartic acid.

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1
Identify the starting materials for the Strecker synthesis. Strecker synthesis involves the reaction of an aldehyde (or ketone), ammonia (NH₃), and hydrogen cyanide (HCN) to form an α-amino nitrile, which is then hydrolyzed to produce an α-amino acid. For aspartic acid, the aldehyde should have a structure that leads to the desired amino acid upon synthesis.
Choose the appropriate aldehyde. Aspartic acid has a carboxylic acid group on both the α and β carbons. Therefore, the starting aldehyde should be oxaloacetaldehyde (CHO-CH₂-COOH), which contains the necessary carbon skeleton.
React the aldehyde with ammonia (NH₃) and hydrogen cyanide (HCN). This step forms an α-amino nitrile intermediate. The reaction mechanism involves the nucleophilic addition of HCN to the aldehyde, followed by the reaction of the resulting imine with NH₃ to form the α-amino nitrile.
Hydrolyze the α-amino nitrile. Treat the α-amino nitrile with aqueous acid (H₃O⁺) or base (OH⁻) to hydrolyze the nitrile group (-C≡N) into a carboxylic acid (-COOH). This step converts the intermediate into aspartic acid.
Verify the structure of the product. Ensure that the final product has the correct structure of aspartic acid, which is HOOC-CH(NH₂)-CH₂-COOH, with both carboxylic acid groups and the amino group in the correct positions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Strecker Synthesis

Strecker synthesis is a method for synthesizing amino acids through the reaction of an aldehyde with ammonia and potassium cyanide. This process involves the formation of an α-amino nitrile intermediate, which can be hydrolyzed to yield the corresponding amino acid. It is particularly useful for producing α-amino acids, such as aspartic acid, from simple starting materials.
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Amino Acids

Amino acids are organic compounds that serve as the building blocks of proteins. They contain an amino group (-NH2), a carboxyl group (-COOH), and a unique side chain (R group) that determines the properties of each amino acid. Aspartic acid is a non-essential amino acid that plays a critical role in the biosynthesis of proteins and is involved in various metabolic processes.
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Hydrolysis

Hydrolysis is a chemical reaction that involves the breaking of a bond in a molecule using water. In the context of Strecker synthesis, hydrolysis converts the α-amino nitrile intermediate into the corresponding amino acid by adding water, which cleaves the nitrile group and forms the carboxylic acid and amino group. This step is essential for obtaining the final product, aspartic acid, from the initial reaction.
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Related Practice
Textbook Question

Give equations for the formation and hydrogenolysis of glutamine benzyl ester.

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Textbook Question

Suggest how you would separate the free L-amino acid from its acylated D enantiomer in Figure 24-5.

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Textbook Question

Show how you would use a Strecker synthesis to make

(b) valine.

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Textbook Question

Give equations for the formation and hydrogenolysis of N-benzyloxycarbonyl methionine.

1
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Textbook Question

Propose a mechanism for each step in the synthesis in part (a).

Textbook Question

Propose a mechanism for each step in the synthesis in part (a).

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