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Chapter 29: Q25P (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

Besides asymmetric hydrogenation (Section 29.4), several other methods are now available for the synthesis of optically active amino acids. How might a reaction like the Strecker synthesis be adapted to the preparation of chiral amino acids?

What types of stabilizing interactions exist between each of the following pairs of amino acids?

a. Ser and Tyr

b. Val and Leu

c. two Phe residues

What aldehyde is needed to synthesize each amino acid by the Strecker synthesis?

(a) Valine;

(b) Leucine;

(c) Phenylalanine.

Question: For the tetra peptide Asp鈥揂rg鈥揤al鈥揟yr:

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

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

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