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Chapter 24: Q9P (page 1268)

Show how the following amino acids might be formed in the laboratory by reductive amination of the appropriate 伪-ketoacid.

Phenylalanine (b) Cysteine (c) Serine (d) Alanine

Short Answer

Expert verified

(a)

Formation of phenylalanine

(b)

Formation of cysteine

(c)

Formation of serine

(d)


Formation of alanine

Step by step solution

01

Reductive amination

The amination that involves the reduction of a carbonyl group to an amine group via the formation of an intermediate amine is referred to as reductive amination.

02

Reaction of ketoacid with ammonia

(a)

The reductive amination of an 伪ketoacid to form phenylalanine is as shown below:

Formation of phenylalanine

(b)

The reductive amination of an 伪ketoacid to form cysteine is as shown below:

Formation of cysteine

(c)

The reductive amination of an 伪ketoacid to form serine is as shown below:

(d)

The reductive amination of an 伪ketoacid to form alanine is as shown below:

Formation of alanine

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Most popular questions from this chapter

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.

Show how you would synthesize Leu-Gly-Ala-Val-Phe starting with Fmoc-Ala-Val-Phe鈥� P

Complete hydrolysis of an unknown basic decapeptide gives Gly, Ala, Leu, Ile, Phe, Tyr, Glu, Arg, Lys, and Ser. Terminal residue analysis shows that the N terminus is Ala, and the C terminus is Ile. Incubation of the decapeptide with chymotrypsin gives two tripeptides, A and B, and a tetrapeptide, C. Amino acid analysis shows that peptide A contains Gly, Glu, Tyr, and; peptide B contains Ala, Phe, and Lys; and peptide C contains Leu, Ile, Ser, and Arg.Terminal residue analysis gives the following results.

Incubation of the decapeptide with trypsin gives a dipeptide D, a pentapeptide E, and a tripeptide F. Terminal residue analysis of F shows that the N terminus is Ser and the C terminus is Ile. Propose a structure for the decapeptide and for fragments A through F.

Draw the electrophoretic separation of Trp, Cys, and His at pH 6.0.

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.

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