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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 鈥揅OOH 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 鈥揅OOH 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 鈥揅OOH group

Synthesis of Phe-Leu.

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Most popular questions from this chapter

Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.

a. Val鈥揋lu

b. Gly鈥揌is鈥揕eu

c. M鈥揂鈥揟鈥揟

What aldehyde is needed to synthesize each amino acid by the Strecker synthesis?

(a) Valine;

(b) Leucine;

(c) Phenylalanine.

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

What is the predominant form of each of the following amino acids at pH=11? What is the overall charge on the amino acid? (a)valine; (b)proline; (c)glutamic acid; (d)lysine?

What is the predominant form of each of the following amino acids at pH=1? What is the overall charge on the amino acid at this pH?(a)threonine ; (b)methionine; (c)aspartic acid; (d)arginine
See all solutions

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