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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

alpha- Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.

a. Draw the structures of the two intermediates formed in this reaction.

b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?

c. What aldehyde is needed to prepare isoleucine?

Show the steps in the synthesis of the tetrapeptide Leu- Phe- Ala- Val

Treatment of a polypeptide with 2-mercaptoethanol yields two polypeptides with the following primary structures:

Val-Met-Tyr-Ala-Cys-Ser-Phe-Ala-Glu-Ser

Ser-Cys-Phe-Lys-Cys-Trp-Lys-Tyr-Cys-Phe-Arg-Cys-Ser

Treatment of the original intact polypeptide with chymotrypsin yields the following peptides:

1. Ala, Glu, Ser 3. Tyr, Val, Met 5. Ser, Phe, 2 Cys, Lys, Ala, Trp

2. 2 Phe, 2 Cys, Ser 4. Arg, Ser, Cys 6. Tyr, Lys

Determine the positions of the disulfide bridges in the original polypeptide.

A professor was preparing a manuscript for publication in which she reported that the pI of the tripeptide Lys-Lys-Lys was 10.6. One of her studentspointed out that there must be an error in her calculations because the pKa of the e-amino group of lysine is 10.8 and the pI of the tripeptide has to begreater than any of its individual pKa values. Was the student correct?

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