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Chapter 24: Q12P (page 1270)

Show how you would use a Strecker synthesis to make

  1. Leucine (b) Valine (c) Aspartic acid

Answer

Short Answer

Expert verified

(a)

Formation of leucine

(b)

Formation of valine

(c)

Formation of aspartic acid

Step by step solution

01

Formation of amino acids by Strecker synthesis

In Strecker synthesis, an aldehyde is treated with ammonia NH3,and then the addition of hydrogen cyanide HCN takes place,followed by hydrolysis H3O+to form the respective amide.

02

(a)

The Strecker synthesis for leucine is shown by the reaction given below:

Formation of leucine

(b)

The Strecker synthesis for valine is shown by the reaction given below:

Formation of valine

(c)

The Strecker synthesis for aspartic acid is shown by the reaction given below:

Formation of aspartic acid

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Most popular questions from this chapter

The herbicide glyphosate(Roundup) kills plants by inhibiting an enzyme needed for synthesis of phenylalanine. Deprived of phenylalanine, the plant cannot make the proteins it needs, and it gradually weakens and dies. Although a small amount of glyphosate is deadly to a plant, its human toxicity is quite low. Suggest why this powerful herbicide has little effect on humans.

Draw the electrophoretic separation of Ala, Lys, and Asp at pH 9.7.

After treatment with peroxyformic acid, the peptide hormone vasopressin is partially hydrolyzed. The following fragments are recovered. Propose a structure for vasopressin.

Phe-Gln-Asn Pro-Arg-Gly.NH2 Cys-Tyr-Phe

Asn-Cys-Pro-Arg Tyr-Phe-Gln-Asn

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.

See all solutions

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