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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

Question: Propose a structure for a compound of molecular formula \({{\bf{C}}_{\bf{7}}}{{\bf{H}}_{{\bf{14}}}}{{\bf{O}}_{\bf{2}}}\) with an IR absorption at \({\bf{1740}}\;{\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\) and the following \({}^{\bf{1}}{\bf{H}}\) NMR data:

\(\begin{array}{*{20}{c}}{{\bf{Absorption}}}&{{\bf{ppm}}}&{{\bf{Relative}}\;{\bf{area}}}\\\hline{{\bf{singlet}}}&{{\bf{1}}{\bf{.2}}}&{\bf{9}}\\{{\bf{triplet}}}&{{\bf{1}}{\bf{.3}}}&{\bf{3}}\\{{\bf{quartet}}}&{{\bf{4}}{\bf{.1}}}&{\bf{2}}\end{array}\)

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Question: For the tetra peptide Asp鈥揂rg鈥揤al鈥揟yr:

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

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

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