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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

a.(S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson’s disease, an inherited defect in copper metabolism.

(R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R) and (S)-penicillamine.

b. What disulfide is formed from oxidation of L-penicillamine?

Which of the following amino acids are typically found in the interior of a globular protein, and which are typically found on the surface: (a)phenylalanine; (b)aspartic acid; (c) lysine; (d) isoleucine; (e) arginine; (f) glutamic acid?

Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:

Glutathione

a. What product is formed when glutathione reacts with an oxidizing agent?

b. What is unusual about the peptide bond between glutamic acid and cysteine?

The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without metabolism, inhibition occurs by reaction of orlistat with a serine residue of the enzyme, forming a covalently bound, inactive enzyme product. Draw the structure of the product formed during inhibition.

Draw the organic products formed in each reaction.

a.

b.
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