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Chapter 29: Q44P (page 1193)

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

Short Answer

Expert verified

Glutamic acid belongs to the amino acid family which is a non-essential amino acid consisting of amino and carboxylic group.It helps in cellular metabolism, improves heartbeat, remove toxic substances.

Step by step solution

01

Glutamic acid

Glutamic acid belongs to the amino acid family which is a non-essential amino acid consisting of amino and carboxylic group.It helps in cellular metabolism, improves heartbeat, remove toxic substances.

02

Mechanism of glutamic acid

In the first step, diethyl acetamidomalonate is treated with Sodium ethoxide, and it forms a compound with the removal of ethanol. In step 2, ethyl acrylate attacks the negatively charged carbon atom and forms a compound as shown below.

Then nucleophile attack to the compound an intermediate is formed in step 3.Finally, it undergoes hydrolysis to form glutamic acid.

Formation of glutamic acid

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Most popular questions from this chapter

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly鈥揂la鈥揝er and Ala鈥揝er鈥揂rg

Histidine is classified as a basic amino acid because one of the N atoms in its five-membered ring is readily protonated by acid. Which N atom in histidine is protonated and why?

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson鈥檚 disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Name each peptide using both the three-letter and one-letter abbreviations of the component amino acids.

What types of stabilizing interactions exist between each of the following pairs of amino acids?

a. Ser and Tyr

b. Val and Leu

c. two Phe residues
See all solutions

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