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Chapter 29: Q41. (page 1193)

Devise a synthesis of threonine from diethyl acetamidomalonate.

Short Answer

Expert verified

Threonine comes under the category of essential amino acids. It is employed in protein biosynthesis. Some food comprising threonine include lentils and cheese.

Step by step solution

01

Threonine

Threonine comes under the category of essential amino acids. It is employed in protein biosynthesis. Some food comprising threonine include lentils and cheese.

02

Diethyl acetamidomalonate

Diethyl acetamidomalonate is employed for various purposes.Several pharmaceutical compounds can be created from diethyl acetamidomalonate

03

Synthesis of threonine from diethyl acetamidomalonate

In the first step, the diethyl acetamidomalonate is treated with sodium ethoxide. This leads to deprotonation of diethyl acetamidomalonate, forming an enolate ion. Alkylation is done with the help of methyl chloride.

This compound is heated in aqueous acid, which results in hydrolysis and decarboxylation, leading to the product threonine.

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Most popular questions from this chapter


Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

Consider two molecules of a tetrapeptide composed of only alanine residues. Draw the hydrogen bonding interactions that result when these two peptides adopt a parallel β-pleated sheet arrangement. Answer this same question for the antiparallel β-pleated sheet arrangement.

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

L-thyroxine, a thyroid hormone and oral medication used to treat thyroid hormone deficiency, is an amino acid that does not exist in proteins. Draw the zwitterionic form of L-thyroxine.

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

(a) Glycine;

(b) Alanine.
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