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Chapter 29: Question 29.71 (page 1197)

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.

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Step by step solution

01

Edman degradation

Edman degradation process deals with determining the amino acids/proteins sequence. It is given by the scientist Pehr Edman. It can determine the sequence from the N-terminal end.

02

Mechanism

Thiazolinone is hydrolyzed from a compound; then, the proton is transferred to the required atom. Finally, on hydrolysis, we get N-phenylthiohydantoin.

N-phenylthiohydantoin mechanism

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Most popular questions from this chapter

Name each peptide using both the three-letter and one-letter abbreviations of the component amino acids.

The enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?

(a)CH3I(b)(CH3)2CHCH2Cl(c)CH3CH2CH(CH3)Br

Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1掳 amines (Section 25.7A).

Question: Identify the functional groups in each molecule. Classify each alcohol, alkyl halide, amide, and amine as 1掳, 2掳, or 3掳

a.

b.

c.

d.

e.

f.

Histidine is classified as a basic amino acid because one of the N atoms in its five-membered ring is readily protonated by acid. Which N atom in histidine is protonated and why?
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