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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 αamino acid as it contains an αamino group and a αcarboxyl 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

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

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

Explain why cyanogens bromide does not cleave on the C-side of cysteine.

a.Which amino acid has the lowest pI value?

b.Which amino acid has the highest pI value?

c.Which amino acid has the greatest amount of negative charge at pH = 6.20?

d.Which amino acid has a greater negative charge at pH = 6.20, glycine or methionine?

A mixture of amino acids that do not separate sufficiently when a single technique is used can often be separated by two-dimensional chromatography.In this technique, the mixture of amino acids is applied to a piece of filter paper and separated by chromatographic techniques. The paper is then rotated90°,and the amino acids are further separated by electrophoresis, producing a type of chromatogram called a fingerprint.Identify the spots in the fingerprint obtainedfrom a mixture of Ser, Glu, Leu, His, Met, and Thr.

Which would have the greatest percentage of polar amino acids, a spherical protein, a cigar-shaped protein, or a subunit of a hexamer? b. Which would have the smallest percentage of polar amino acids?
See all solutions

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