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Chapter 29: Q44. (page 1193)

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

Short Answer

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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

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

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

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

  1. Why does a -nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation?
  2. Would a -methoxyphenyl ester perform the same function? Why or why not?

Use the given experimental data to deduce the sequence of an octapeptide that contains the following amino acids: Ala, Gly (2 equiv), His (2 equiv), Ile, Leu and Phe. Edman degradation cleaves Gly from the octapeptide, and carboxypeptidase forms Leu and a heptapeptide. Partial hydrolysis forms the following fragments: Ile-His-Leu, Gly, Gly-Ala-Phe-His, and Phe-His-Ile.

a.(S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson’s disease, an inherited defect in copper metabolism.

(R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R) and (S)-penicillamine.

b. What disulfide is formed from oxidation of L-penicillamine?

Which of the following amino acids are typically found in the interior of a globular protein, and which are typically found on the surface: (a)phenylalanine; (b)aspartic acid; (c) lysine; (d) isoleucine; (e) arginine; (f) glutamic acid?

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s 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.
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