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Chapter 21: Q24P (page 1002)

What amino acid is formed when the aldehyde used in the Strecker synthesis is

a. acetaldehyde? b. 2-methylbutanal? c. 3-methylbutanal?

Short Answer

Expert verified

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

Step by step solution

01

Strecker synthesis

In Strecker synthesis, an aldehyde reacts with ammonia to form an imine. A nucleophilic addition reaction with cyanide ion forms an intermediate, which, when hydrolyzed, forms the amino acid.

02

Formation of respective amino acids

a)

Treatment of acetaldehyde with HCN produces the corresponding 伪-aminonitrile which upon hydrolysis produces alanine. The reaction is as follows:

b)

Treatment of 2-methyl butanal with HCN produces the corresponding -amino nitrile which upon hydrolysis produces isoleucine. The reaction is as follows:

c)

Treatment of 3-methyl butanal with HCN produces the corresponding 伪-aminonitrile which upon hydrolysis produces leucine. The reaction is as follows:

Formation of leucine (c)

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Most popular questions from this chapter

Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate the peptide bonds.

Alanine has pKa values of 2.34 and 9.69. Therefore, alanine exists predominately as a zwitterion in an aqueous solution with pH > ____ and pH < ____.

Glutathione is a tripeptide whose function is to destroy harmful oxidizing agents in the body. Oxidizing agents are bought to be responsible for some of the effects of aging and to play a causative role in cancer.

Glutathione removes oxidizing agents by reducing them. In the process, glutathione is oxidized, resulting in the formation of a disulphide bond between two glutathione molecules. An enzyme subsequently reduces the disulphide bond, returning glutathione to its original condition so it can react with another oxidizing agent.

a. What amino acids make up glutathione?

b. What is unusual about glutathione鈥檚 structure?

a. Which isomer鈥�(R)-alanine or (S)-alanine鈥攊s d-alanine?

b. Which isomer鈥�(R)-aspartate or (S)-aspartate鈥攊s d-aspartate?

c. Can a general statement be made relating R and S to d and l?

Explain the difference in the \({\bf{p}}{{\bf{K}}_{\bf{a}}}\) values of the carboxyl groups of alanine, serine, and cysteine.
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