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Chapter 29: 24P (page 1177)

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

Short Answer

Expert verified

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

The structure of the required dipeptide is as shown:

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:

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.

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Most popular questions from this chapter

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?

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

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

(a) Valine;

(b) Leucine;

(c) Phenylalanine.

Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin,

appeared in Section 22.6B.)

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?
See all solutions

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