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Chapter 24: Q16P. (page 1273)

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

Short Answer

Expert verified

Formation of N- benzyloxy carbonyl methionine

Hydrogenolysis of N-benzyloxy carbonyl methionine

Step by step solution

01

Acylation process

Anamino group is converted to an amide with the help of an acylating agent. In order to protect the amino group from unwanted nucleophilic substitution reactions, the acylation process is carried out. A large number of acid chlorides and anhydrides are used for acylation. The amino group is acylated by benzyl chloroformate to yield a benzyloxycarbonyl derivative, which is often used as a protecting group in peptide synthesis.

02

(a)

The equation for the formation of benzyloxycarbonyl methionine is as shown below:

Formation of N-benzyloxy carbonyl methionine

(b)

The equation for the hydrogenolysis of benzyloxycarbonyl methionine is as shown below:

Hydrogenolysis of N-benzyloxy carbonyl methionine

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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.

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

Show how you would use bromination followed by amination to synthesize the following amino acids.

  1. Glycine (b) Leucine (c) Glutamic acid

Draw the complete structures of the following peptides:

(a) Thr-Phe-Met (b) Serylarginylglycylphenylalanine (c) IMQDK (d) ELVIS

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

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