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Chapter 24: Q15P. (page 1272)

Give equations for the formation and hydrogenolysis of the glutamine benzyl ester

Short Answer

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Formation of glutamine benzyl ester

Hydrogenolysis of glutamine benzyl ester

Step by step solution

01

Benzyl esters

Benzyl esters are extremely useful as protecting groups asthey can be removed by acid hydrolysis or neutral hydrogenolysis. Hydrogenolysis implies breaking apart withthe addition of hydrogen. Benzyl ester is cleaved by catalytic hydrogenation, which converts the benzyl group to toluene,thus leaving the deprotected amino acid.

02

Equation for formation and hydrogenolysis

The equation for the formation of glutamine benzyl ester is shown below:

Formation of glutamine benzyl ester

The equation for the hydrogenolysis of glutamine benzyl ester is as shown below:

Hydrogenolysis of glutamine benzyl ester

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Most popular questions from this chapter

Aspartame(Nutrasweetยฎ) is a remarkably sweet-tasting dipeptide ester. Complete hydrolysis of aspartame gives phenylalanine, aspartic acid, and methanol. Mild incubation with carboxypeptidase has no effect on aspartame. Treatment of aspartame with phenyl isothiocyanate, followed by mild hydrolysis, gives the phenylthiohydantoin of aspartic acid. Propose a structure for aspartame.

Show the steps and intermediates in the synthesis of Leu-Ala-Phe by the solid-phase process.

The herbicide glyphosate(Roundup) kills plants by inhibiting an enzyme needed for synthesis of phenylalanine. Deprived of phenylalanine, the plant cannot make the proteins it needs, and it gradually weakens and dies. Although a small amount of glyphosate is deadly to a plant, its human toxicity is quite low. Suggest why this powerful herbicide has little effect on humans.

Show how the following amino acids might be formed in the laboratory by reductive amination of the appropriate ฮฑ-ketoacid.

Phenylalanine (b) Cysteine (c) Serine (d) Alanine

Draw the structure of the predominant form of

(a)Isoleucine at pH 11 (b) Proline at pH 2

(c)Arginine at pH 7 (d) Glutamic acid at pH 7

A mixture of alanine, lysine, and aspartic acid at 1). pH 6 ; 2). pH 11; 3). pH 2
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