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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

The Sanger method for N-terminus determination is a less common alternative to the Edman degradation. In the Sanger method, the peptide is treated with the Sanger reagent, 2,4-dinitrofluorobenzene, and then hydrolyzed by reaction with 6 M aqueous HCl. The N-terminal amino acid is recovered as its 2,4-dinitrophenyl derivative and identified.

(a)Propose a mechanism for the reaction of the N terminus of the peptide with 2,4-dinitrofluorobenzene.

(b) Explain why the Edman degradation is usually preferred over the Sanger method.

Draw the electrophoretic separation of Trp, Cys, and His at pH 6.0.

Show how you would use a Strecker synthesis to make

  1. Leucine (b) Valine (c) Aspartic acid

Answer

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?

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.

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