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Chapter 29: 62P (page 1196)

Write out the steps for the synthesis of each peptide using the Merrifield method:

(a)Ala-Leu-Phe-Phe;

(b) Phe-Gly-Ala-Ile.

Short Answer

Expert verified

Merrifield method is a method developed by Bruce Merrifield, and it requires connecting the C-terminus of the peptide chain with a solid in polymeric form. In this method, the product is purified at every step to avoid unwanted cross-reactions.

Step by step solution

01

Merrifield Method

Merrifield method is a method developed by Bruce Merrifield, and it requires connecting the C-terminus of the peptide chain with a solid in polymeric form. In this method, the product is purified at every step to avoid unwanted cross-reactions.

02

Synthesis of Ala-Leu-Phe-Phe

First of all, make all the Fmoc derivatives for amino acids. The steps for the synthesis of Ala-Leu-Phe-Phe are shown as,

Synthesis of Ala-Leu-Phe-Phe

03

Synthesis of Phe-Gly-Ala-Ile

Firstly, make all the Fmoc derivatives for amino acids. The steps for the synthesis of Phe-Gly-Ala-Ile are shown as,

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Most popular questions from this chapter

a. Draw the structure of the tripeptide A-A-A, and label the two ionizable functional groups.

b. What is the predominant form of A-A-A at pH=1?

c. ThepKa values for the two ionizable functional groups (3.39 and 8.03) differ considerably from thepKa values of alanine (2.35 and 9.87;see table 29.1). Account for the observedpKa differences.

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

Brucine is a poisonous alkaloid obtained from Strychnosnux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme similar to the one given in Section 29.3A, which shows how a racemic mixture of phenylalanine can be resolved using brucine

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

Draw the organic products formed in each reaction.
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