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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

The enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?

(a)CH3I(b)(CH3)2CHCH2Cl(c)CH3CH2CH(CH3)Br

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.

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

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

Which of the following amines can be used to resolve a racemic mixture of amino acids?

(a)

(b)

(c)

(d)
See all solutions

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