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Chapter 29: Q24. (page 1177)

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

Short Answer

Expert verified

Protecting Group

Synthesis of Ala-Ser

Step by step solution

01

The given dipeptide

The given dipeptide has two amino acids, - alanine, and serine.

The structure of the required dipeptide is as shown:

Dipeptide

02

Protecting amine and carboxylic acid groups

The amine group in alanine is protected by using Boc(tertiary butyloxy carbonyl) reagent. The carboxylic acid group in serine is protected with bezyl alcohol as benzyl ester.

03

Synthesis

The amino acid alanine with a protected amino group, and the amino acid serine with a protected carboxylic acid group will react with each other and form the required dipeptide.

Protecting Groups

Synthesis of Ala-Ser

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Most popular questions from this chapter

How many different tripeptides can be formed from three different amino acids?

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

(a)Ala-Leu-Phe-Phe;

(b) Phe-Gly-Ala-Ile.

Draw the organic products formed in each reaction.

Use the given experimental data to deduce the sequence of an octapeptide that contains the following amino acids: Ala, Gly (2 equiv), His (2 equiv), Ile, Leu and Phe. Edman degradation cleaves Gly from the octapeptide, and carboxypeptidase forms Leu and a heptapeptide. Partial hydrolysis forms the following fragments: Ile-His-Leu, Gly, Gly-Ala-Phe-His, and Phe-His-Ile.

What α- halo carbonyl compoundis needed to synthesize each amino acid?

(a) Glycine

(b) Isoleucine

(c) Phenylalanine
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