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Chapter 29: Q65. (page 1197)

Draw the mechanism for the reaction that removes an Fmoc group from an amino acid under the following conditions:

Short Answer

Expert verified

Reaction mechanism constitutes a step-by-step explanation of what happens in a particular reaction. The elementary process comprises the term used to indicate each specific reaction step.

Step by step solution

01

Reaction mechanism

Reaction mechanism constitutes a step-by-step explanation of what happens in a particular reaction. The elementary process comprises the term used to indicate each specific reaction step.

02

F moc group

F moc group constitutes an amino protecting group, which comprises 9-fluorenylmethoxycarbonyl and is created by combining amino acid with 9-fluorenylmethyl chloroformate. The F moc group can be removed using a base like NH3 or an amine .

03

Mechanism for the reaction that removes a Fmoc group from an amino acid

The piperidine abstracts an acidic proton from the starting material. This generates a negative charge on the carbon atom. The conjugation of the negative charge eliminates the carbon dioxide in the next step.

The protonation of the amino group follows this. The final step involves the proton transfer from the acid to an imine leading to the final product. The mechanism can be given as:

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Most popular questions from this chapter

Draw all the steps in the synthesis of each peptide from individual amino acids:

  1. Gly-Ala;

  2. Ile-Ala-Phe

Question:With reference to the following peptide:

(a) Identify the N-terminal and C-terminal amino acids.

(b) Name the peptide using one-letter abbreviations.

(c) Label all the amide bonds in the peptide backbone.

As shown in Mechanism 29.2, the final steps in the Edman degradation result in rearrangement of a thiazolinone to an N-phenylthiohydantoin. Draw a stepwise mechanism for this acid-catalyzed reaction.

What types of stabilizing interactions exist between each of the following pairs of amino acids?

a. Ser and Tyr

b. Val and Leu

c. two Phe residues

Brucine is a poisonous alkaloid obtained from Strychnosnux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme similar to the one given in Section 29.3A, which shows how a racemic mixture of phenylalanine can be resolved using brucine
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