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Chapter 29: Q43. (page 1193)

Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1掳 amines (Section 25.7A).

Short Answer

Expert verified

Compound B which is N-alkylation is an intermediate of this reaction.

Step by step solution

01

Gabriel synthesis

In Gabriel synthesis, reaction is altered from primary alkyl halides to primary amines. It was named by Siegmund Gabriel who was a German chemist.Here, in this reaction, over alkylation is avoided.

02

Synthesis of primary amine

When diethyl adipate is treated with bromine followed by acetic acid, itgives Br-CH(COOEt)2 , and when it is treated with potassiumphthalimide, it forms a Nitrogen alkylation.

Nitrogen alkylation is an intermediate that reacts with NaoEt and ClCH2CH2SCH3forms a compound C which on further reaction with sodium hydroxide followed by hydrolysis under heat forms a product.

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Most popular questions from this chapter

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

a.

b.

Write out the steps for the synthesis of each peptide using the Merrifield method:

(a)Ala-Leu-Phe-Phe;

(b) Phe-Gly-Ala-Ile.

How many different tripeptides can be formed from three different amino acids?

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?

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
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