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Chapter 29: 24P (page 1177)

Devise a synthesis of the following dipeptide from amino acid starting materials.

Short Answer

Expert verified

The given dipeptide has two amino acids, - alanine, and serine.

The structure of the required dipeptide is as shown:

Step by step solution

01

The given dipeptide

The given dipeptide has two amino acids, - alanine, and serine.

The structure of the required dipeptide is as shown:

02

Protecting amine and carboxylic acid groups

The amine group in alanine is protected by using Boc(tertiary butyloxy carbonyl) reagent. The carboxylic acid group in serine is protected with bezyl alcohol as benzyl ester.

03

Synthesis

The amino acid alanine with a protected amino group, and the amino acid serine with a protected carboxylic acid group will react with each other and form the required dipeptide.

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Most popular questions from this chapter

Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:

a. What product is formed when glutathione reacts with an oxidizing agent?

b. What is unusual about the peptide bond between glutamic acid and cysteine?

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly–Ala–Ser and Ala–Ser–Arg

Draw the products of each reaction.

(a)

(b)

(c)

(d)

Give the amino acid sequence of each peptide using the fragments obtained by partial hydrolysis of the peptide with acid.

  1. A tetrapeptide that contains Ala, Gly, His, and Tyr, which is hydrolyzed to the dipeptides His-Tyr, Gly-Ala, and Ala-His.
  2. A pentapeptide that contains Glu, Gly, His, Lys, and Phe, which is hydrolyzed to His-Gly-Glu, Gly-Glu-Phe, and Lys-His.

For the tetra peptide Asp–Arg–Val–Tyr:

a. Name the peptide using one-letter abbreviations.

b. Draw the structure.

c. Label all amide bonds.

d. Label the N-terminal and C-terminal amino acids
See all solutions

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