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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 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.

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly–Ala–Ser and Ala–Ser–Arg

What is the structure of each amino acid at its isoelectric point: (a) alanine (b) methionine; (c)aspartic acid; (d) lysine?

What form exists at the isoelectric point of each of the following amino acids: (a) valine; (b)leucine; (c)proline; (d) glutamic acid

The fibroin proteins found in silk fibers consist of large regions of β-pleated sheets stacked one on top of another. (a) Explain why having a glycine at every other residue allows the β-pleated sheets to stack on top of each other. (b) Why are silk fibers insoluble in water?
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