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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.)

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?

(a) What products are formed when each peptide is treated with trypsin? (b) What products are formed when each peptide is treated with chymotrypsin?

[1] Gly–Ala–Phe–Leu–Lys–Ala

[2] Phe–Tyr–Gly–Cys–Arg–Ser

[3] Thr–Pro–Lys–Glu–His–Gly–Phe–Cys–Trp–Val–Val–Phe


Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

What alkyl halide is needed to synthesize each amino acid from diethyl acetamidomalonate: (a)Asn; (b)His; (c)Trp?
See all solutions

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