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Chapter 29: Q42P (page 1193)

Devise a synthesis of each amino acid from acetaldehyde (CH3CHO):

(a) Glycine;

(b) Alanine.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Amino acid

Amino acid plays a vital role in body functions such as tissue repairing, digesting food, and enzyme formation.It is a white crystalline solid that dissolves in water.

02

Synthesis of amino acid

(a) When acetaldehyde is treated with bromine followed by acetic acid, it gives acetyl bromide. Acetyl bromide is then treated withCrO3 followed by sulphuric acid, and it gives bromoacetic acid which on further treatment with excess of NH3forms glycine.

Formation of glycine

(b) When acetaldehyde is treated with ammonium chloride and sodium cyanide, followed by hydrolysis, alanine is formed.

Formation of alanine

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Most popular questions from this chapter

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.

Write out a scheme for the resolution of the two enantiomers of the antiplatelet drug clopidogrel with 10-camphorsulfonic acid.

Clopidogrel 10-camphorsulfonic acid

Give the amino acid sequence of each peptide using the fragments obtained by partial hydrolysis of the peptide with acid.

  1. A tetrapeptide that contains Ala, Gly, His, and Tyr, which is hydrolyzed to the dipeptides His-Tyr, Gly-Ala, and Ala-His.
  2. A pentapeptide that contains Glu, Gly, His, Lys, and Phe, which is hydrolyzed to His-Gly-Glu, Gly-Glu-Phe, and Lys-His.

Draw the organic products formed in each reaction.

a.

b.

With reference to the following peptide:

(a) Identify the N-terminal and C-terminal amino acids.

(b) Name the peptide using one-letter abbreviations.

(c) Label all the amide bonds in the peptide backbone.
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