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Chapter 29: Q19. (page 1170)

Draw the structure of the N-phenylthiohydantoin formed by initial Edman degradation of each peptide: (a) Ala-Gly-Phe-Phe; (b) Val-Ile-Tyr.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Edman Degradation

Edman degradation is a technique to cleave amino acids from the N-terminal of the peptide chain, and the process continues until the whole sequence is known.

There are two products formed by Edman degradation, one is N-phenylthiohydantoin, and the other is a new peptide chain with one less amino acid.

02

Structure of the N-phenylthiohydantoin formed by initial Edman degradation of Ala-Gly-Phe-Phe.

(a) The initial Edman degradation of Ala-Gly-Phe-Phe is done by cleaving amino acid from N-terminal.


Structure of N-phenylthiohydantoin


03

Structure of the N-phenylthiohydantoin formed by initial Edman degradation of Val-Ile-Tyr.

(b) The initial Edman degradation of Val-Ile-Tyr is done by removing N-terminal amino acid from the peptide chain.


Structure of N-phenylthiohydantoin

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Most popular questions from this chapter

Draw the organic products formed in each reaction.

Write out a stepwise sequence that shows how a racemic mixture of leucine enantiomers can be resolved into optically active amino acids using (R)-伪-methylbenzylamine.

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

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.
See all solutions

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