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Chapter 29: Q31. (page 1192)

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

Short Answer

Expert verified

Protecting Amine Group

Protecting –COOH group.

Synthesis of Phe-Leu.

Step by step solution

01

Synthesis of Dipeptide

The general synthesis of dipeptide involves the reaction between two amino acids. The C-terminal and N-terminal amino acids can be identified based on the required dipeptide.

The respective functional groups can be protected by using suitable reagents and reacting.

02

The required dipeptide structure

The structure of the Phe-Leu dipeptide is as shown below:

It has N-terminal phenylalanine and C-terminal Leucine.

So, the amine group in phenylalanine and the –COOH group of Leucine should be protected with the reagents Boc and benzyl alcohol, respectively.

03

 Synthesis

The synthesis of Phe-Leuinvolves the below-shown steps:

Protecting Amine Group

Protecting –COOH group

Synthesis of Phe-Leu.

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Most popular questions from this chapter

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

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

Draw the product formed when the following amino acid is treated with each reagent: (a)CH3OH;H+; (b)CH3COCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e)C6H5N=C=S.

Histidine is classified as a basic amino acid because one of the N atoms in its five-membered ring is readily protonated by acid. Which N atom in histidine is protonated and why?
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