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Chapter 29: Q25. (page 1179)

Outline the steps needed to synthesize the tetrapeptideAla–Leu–Ile–Gly 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

Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin,

appeared in Section 22.6B.)

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

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?

Besides the Boc and Fmoc protecting groups used in peptide synthesis, amines can also be protected by reaction with benzyl chloroformate (C6H5CH2OCOCl). Draw the structure of the product formed by reaction of alanine with benzyl chloroformate

Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1° amines (Section 25.7A).
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