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Chapter 29: Q41P (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

Step 1: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.

Synthesis of threonine from diethyl acetamidomalonate

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Most popular questions from this chapter

Another method to form a peptide bond involves a two-step process:

[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.

[2] Reaction of the p-nitrophenyl ester with an amino acid ester.

  1. Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation?

  2. Would a p-methoxyphenyl ester perform the same function? Why or why not?

Explain why the pKaof the -NH3+group of an α-amino acid is lower than the pKaof the ammonium ion derived from a 1∘amine (RNH3+). For example, thepKa of therole="math" localid="1648617659352" -NH3+ group of alanine is 9.87 but thepka ofCH3NH3+ is 10.63.

Devise a stepwise synthesis of the tripeptide Val-leu-Val from 3-methylbutanal[CH32CHCH2CHO] as the only organic starting material. You may also use any required inorganic or organic reagents.

What alkene is needed to synthesize each amino acid by an enantioselective hydrogenation reaction using and :

(a) Alanine;

(b) Leucine;

(c) Glutamine?

Glutamic acid is synthesized by the following reaction sequence. Draw a stepwise mechanism for Steps [1]–[3].
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