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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]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

Identify A鈥揈 in the following reaction sequence.

Question: Identify the nucleophile and the electrophile in the following acid鈥揵ase reactions:

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 鈥渁ctivate鈥� the carboxy group of the first amino acid to amide formation?
  2. Would a -methoxyphenyl ester perform the same function? Why or why not?

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 鈥渁ctivate鈥� 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?

Draw the organic products formed in each reaction.
See all solutions

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