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Chapter 21: Q23P (page 1002)

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

Short Answer

Expert verified

Formation of phenylalanine

Step by step solution

01

Ester synthesis

α-Bromomalonic ester and potassium phthalimide undergo an SN2 reaction. A proton is easily removed from the a-carbon of N-phthalimidomalonic ester because it is flanked by two carbonyl groups. The resulting carbanion undergoes an SN2reaction with an alkyl halide.

02

Preparation of given amino acid

a)

4-Bromo-1-butanamine is used in the acetamido malonic ester syntheses to prepare lysine which is given as follows:

b)

Benzyl bromide is used in the acetamido malonic ester synthesis to prepare phenylalanine which is represented as follows:

Formation of phenylalanine (b)

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Most popular questions from this chapter

Show how aspartame can be synthesized using DCCD.

Why are the carboxylic acid groups of the amino acids more acidic

(pKa ~ 2) than a carboxylic acid such as acetic acid (pKa = 4.76)?

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%?

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?

Draw the form of aspartate that predominates at the following pH values:

a. pH = 1.0 b. pH = 2.6 c. pH = 6.0 d. pH = 11.0
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