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Chapter 24: Q14P (page 1272)

Question: Propose a mechanism for the acid-catalyzed hydrolysis of phenylalanine ethyl ester.

Short Answer

Expert verified

Esters of amino acids can be used as protected derivatives in order to prevent the carboxyl group from reacting in an unusual manner. The most common protecting groups are methyl, ethyl and benzyl estersA

Step by step solution

01

Step-by-Step solutionStep 1: Esterification of carboxyl group

Esters of amino acids can be used as protected derivatives in order to prevent the carboxyl group from reacting in an unusual manner. The most common protecting groups are methyl, ethyl and benzyl estersA

02

Mechanism

Ester is hydrolyzed by the aqueous acid which regenerates the free amino acid.

Mechanism for acid-catalyzed hydrolysis of phenylalanine ethyl ester to phenylalanine

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Most popular questions from this chapter

There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The following method converts the acid to an N-hydroxysuccinimide (NHS) ester.

(a) Explain why an NHS ester is much more reactive than a simple alkyl ester.

(b) Propose a mechanism for the reaction shown.

(c) Propose a mechanism for the reaction of the NHS ester with an amine, R-NH2

Draw the electrophoretic separation of Ala, Lys, and Asp at pH 9.7.

Most naturally occurring amino acids have chiral centers (the asymmetric α carbon atoms) that are named (S) by the Cahn-Ingold-Prelog convention (Section 5-3). The common naturally occurring form of cysteine has a chiral center that is named (R), however.

(a) What is the relationship between (R)-Cysteine and (S)-alanine? Do they have the opposite three-dimensional configuration (as the names might suggest) or the same configuration?

(b) (S)-Alanine is an L-amino acid (Figure 24-2). Is (R)-cysteine a D-amino acid or an L-amino acid?

Sometimes chemists need the unnatural D enantiomer of an amino acid, often as part of a drug or an insecticide. Most L-amino acids are isolated from proteins, but the D-amino acids are rarely found in natural proteins. D-amino acids can be synthesized from the corresponding L-amino acids. The following synthetic scheme is one of the possible methods.

(a) Draw the structures of intermediates 1 and 2 in this scheme.

(b) How do we know that the product is entirely the unnatural D configuration?

Give equations for the formation and hydrogenolysis of N-benzyloxy carbonyl methionine.
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