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Chapter 24: Q15P. (page 1272)

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

Short Answer

Expert verified

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

Draw the structure of the phenylthiohydantoin derivatives of

(a) Alanine (b) Tryptophan (c) Lysine (d) proline

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

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

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?

Complete hydrolysis of an unknown basic decapeptide gives Gly, Ala, Leu, Ile, Phe, Tyr, Glu, Arg, Lys, and Ser. Terminal residue analysis shows that the N terminus is Ala, and the C terminus is Ile. Incubation of the decapeptide with chymotrypsin gives two tripeptides, A and B, and a tetrapeptide, C. Amino acid analysis shows that peptide A contains Gly, Glu, Tyr, and; peptide B contains Ala, Phe, and Lys; and peptide C contains Leu, Ile, Ser, and Arg.Terminal residue analysis gives the following results.

Incubation of the decapeptide with trypsin gives a dipeptide D, a pentapeptide E, and a tripeptide F. Terminal residue analysis of F shows that the N terminus is Ser and the C terminus is Ile. Propose a structure for the decapeptide and for fragments A through F.

A molecular weight determination has shown that an unknown peptide is a pentapeptide, and an amino acid analysis shows that it contains the following residues: one Gly, two Ala, one Met, one Phe. Treatment of the original pentapeptide with carboxypeptidase gives alanine as the first free amino acid released. Sequential treatment of the pentapeptide with phenyl isothiocyanate followed by mild hydrolysis gives the following derivatives:

Propose a structure for the unknown pentapeptide.
See all solutions

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