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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

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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

Question:Draw the product formed when the following amino acid is treated with each reagent: (a) CH3OH;H+ (b) CH3COCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e).C6H5N=C=S

Question: Identify A and B, isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\), from the given \({}^{\bf{1}}{\bf{H}}\)NMR data: Compound A exhibits signals at 1.75 (doublet, 3H,\({\bf{J = 6}}{\bf{.9 Hz}}\)) and 5.89 (quartet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 6}}{\bf{.9 Hz}}\)) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 1}}{\bf{.9 Hz}}\)), and 5.59 (doublet, \({}^{\bf{1}}{\bf{H}}\), \({\bf{J = 1}}{\bf{.9 Hz}}\)) ppm.

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

  1. Gly-Ala;

  2. Ile-Ala-Phe

Write out the steps for the synthesis of each peptide using the Merrifield method:

  1. Ala-Leu-Phe-Phe; (b) Phe-Gly-Ala-Ile.

Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin,

appeared in Section 22.6B.)
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