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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

Draw the structure for each peptide:

(a) Phe鈥揂la;

(b) Gly鈥揋ln;

(c) Lys鈥揋ly;

(d) R-H

Devise a synthesis of threonine from diethyl acetamidomalonate.

Consider two molecules of a tetrapeptide composed of only alanine residues. Draw the hydrogen bonding interactions that result when these two peptides adopt a parallel 尾-pleated sheet arrangement. Answer this same question for the antiparallel 尾-pleated sheet arrangement.

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

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?
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