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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. Calculate the overall yield of bradykinin when the yield for the addition of each amino acid to the chain is 70%.

b. What would be the overall yield of a peptide containing 15 amino acids if the yield for the incorporation of each is 80%?

Draw the predominant form for glutamate in a solution with the following pH:

a. 0 b. 3 c. 6 d. 11

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

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

Cells can also convert a-keto acids into amino acids, but because the reagents organic chemists use for this reaction are not available in cells, they carry out this reaction by a different mechanism

(a) What amino acid is obtained from the reductive amination of each of the following metabolic intermediates in a cell by reductive amination?



(b)What amino acids are obtained from the same metabolic intermediates when the amino acids are synthesized in the laboratory?

What alkyl halide is used in the acetamidomalonic ester synthesis to prepare a. lysine? b. phenylalanine?
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