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Chapter 29: Q25. (page 1179)

Outline the steps needed to synthesize the tetrapeptideAla鈥揕eu鈥揑le鈥揋ly using the Merrifield technique.

Short Answer

Expert verified

The synthesis of long peptides can be done by using Merrifield technique. It is a solid-phase technique.

An amino acid is attached to an insoluble polymer in the Merrifield method. Amino acids are sequentially added, one at a time, thereby forming successive peptide bonds.

Because impurities and by-products are not attached to the polymer chain, they are removed simply by washing them away with a solvent at each stage of the synthesis.

Step by step solution

01

Merrifield technique

The synthesis of long peptides can be done by using Merrifield technique. It is a solid-phase technique.

An amino acid is attached to an insoluble polymer in the Merrifield method. Amino acids are sequentially added, one at a time, thereby forming successive peptide bonds.

Because impurities and by-products are not attached to the polymer chain, they are removed simply by washing them away with a solvent at each stage of the synthesis.

02

Al-Leu-Ile-Gly

The given peptide has four amino acids in it. Hence it is an example of a tetrapeptide. The amino acids are alanine, leucine, isoleucine, and glycine.

03

Synthesis of the given tripeptide

The detailed synthesis of the given tetrapeptide in the solid phase is as shown below:

Synthesis of the given tetrapeptide

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Most popular questions from this chapter

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.

Question: Identify the functional groups in each molecule. Classify each alcohol, alkyl halide, amide, and amine as 1掳, 2掳, or 3掳

a.

b.

c.

d.

e.

f.

Draw the structure of the N-phenylthiohydantoin formed by initial Edman degradation of each peptide: (a) Ala-Gly-Phe-Phe; (b) Val-Ile-Tyr.

Tryptophan is not classified as a basic amino acid even though it has a heterocycle containing a nitrogen atom. Why is the N atom in the five-membered ring of tryptophan not readily protonated by acid?

Draw the structure for each peptide:

(a) Phe鈥揂la;

(b) Gly鈥揋ln;

(c) Lys鈥揋ly;

(d) R-H
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