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Chapter 21: Q22P (page 1002)

What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following alkyl halides are used in the third step?

(a)

(b)CH3SCH2CH2Br

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Ester synthesis

Amino acids can be synthesized with better yields than those obtained by the previous two methods (HVZ reaction and reductive amination) via an N-phthalimidomalonic ester synthesis, a method that combines the malonic ester synthesis and the Gabriel synthesis.

02

Formation of respective amino acids

Leucine is an essential amino acid that is used in the biosynthesis of proteins. It is anamino acid as it contains an amino group and a carboxyl group. The mechanism of the reaction is represented as follows:

Formation of Leucine

Methionine is formed by the reaction of ester with the given alkyl halide. The mechanism of the reaction is represented as follows:

Formation of methionine

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Most popular questions from this chapter

a. Which isomer鈥�(R)-alanine or (S)-alanine鈥攊s d-alanine?

b. Which isomer鈥�(R)-aspartate or (S)-aspartate鈥攊s d-aspartate?

c. Can a general statement be made relating R and S to d and l?

Do any other amino acids in Table 21.2 have more than one asymmetric center?

The aldonic acid of D-glucose forms a five-membered-ring lactone. Draw its structure.

What amino acid is formed when the aldehyde used in the Strecker synthesis is

a. acetaldehyde? b. 2-methylbutanal? c. 3-methylbutanal?

Draw the product obtained when a lysine side chain in a polypeptide reacts with maleic anhydride.
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