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Chapter 24: Q11P. (page 1270)

  1. Show how you would use a Strecker synthesis to make phenylalanine.
  2. Propose a mechanism for each step in the synthesis in part (a).

Short Answer

Expert verified

(a)

Formation of phenylalanine

(b)

Formation of protonated amine

Addition of CN group

Formation of phenylalanine

Step by step solution

01

Strecker synthesis

A large number of amino acids can be formed from appropriate aldehydes by a process known as Strecker synthesis. In this synthesis, an aldehyde is treated with ammonia NH3and hydrogen cyanide HCN,followed by hydrolysis H3O+.

02

(a)

The Strecker synthesis ofalanine is shown by the reaction shown below:

Formation of phenylalanine

(b)

The mechanism for each step in the synthesis of phenylalanine is shown below:

Addition of CN group

Formation of phenylalanine

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Most popular questions from this chapter

Show the third and fourth steps in the sequencing of oxytocin. Use figure 24-14 as a guide.

The Sanger method for N-terminus determination is a less common alternative to the Edman degradation. In the Sanger method, the peptide is treated with the Sanger reagent, 2,4-dinitrofluorobenzene, and then hydrolyzed by reaction with 6 M aqueous HCl. The N-terminal amino acid is recovered as its 2,4-dinitrophenyl derivative and identified.

(a)Propose a mechanism for the reaction of the N terminus of the peptide with 2,4-dinitrofluorobenzene.

(b) Explain why the Edman degradation is usually preferred over the Sanger method.

Sometimes chemists need the unnatural D enantiomer of an amino acid, often as part of a drug or an insecticide. Most L-amino acids are isolated from proteins, but the D-amino acids are rarely found in natural proteins. D-amino acids can be synthesized from the corresponding L-amino acids. The following synthetic scheme is one of the possible methods.

(a) Draw the structures of intermediates 1 and 2 in this scheme.

(b) How do we know that the product is entirely the unnatural D configuration?

Daw the structure of the predominant form of

Isoleucine at pH 11 (b) Proline at pH 2

Arginine at pH 7 (d) Glutamic acid at pH 7

A mixture of alanine, lysine, and aspartic acid at 1). pH 6 ; 2). pH 11; 3). pH

Draw the structure of the predominant form of

(a)Isoleucine at pH 11 (b) Proline at pH 2

(c)Arginine at pH 7 (d) Glutamic acid at pH 7

A mixture of alanine, lysine, and aspartic acid at 1). pH 6 ; 2). pH 11; 3). pH 2
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