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Chapter 21: Q 22P (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

Answer:

(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 an 伪amino acid as it contains an 伪amino group and a 伪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

Which is the more effective buffer at physiological pH, a solution of 0.1 M glycylglycine or a solution of 0.2 M glycine?

In what order would histidine, serine, aspartate, and valine be eluted with a buffer of pH 4 from a columncontaining an anion-exchange resin (Dowex 1)?

Esterase is an enzyme that catalyzes the hydrolysis of esters. It hydrolyzes esters of L-amino acids more rapidly than esters of D-amino acids. How can this enzyme be used to separate a racemic mixture of amino acids?

Calculate the pI of each of the following amino acids:

a.asparagine b. arginine c. serine d. aspartate

Explain the order of elution (with a buffer of pH 4) of the following pairs of amino acids through a column packed with Dowex 50 (Figure 21.3):

a. aspartate before serine c. valine before leucine

b. serine before alanine d. tyrosine before phenylalanine
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