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Chapter 29: 19P (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

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.

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.

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.

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Most popular questions from this chapter

Question: Draw the other three stereoisomers of L-isoleucine, and label the stereogenic centers as R or S.

Devise a synthesis of each peptide from amino acid starting materials:

(a) Leu–Val; (b) Ala–Ile–Gly.

Explain why the pKaof the -NH3+group of an α-amino acid is lower than the pKaof the ammonium ion derived from a 1°amine (RNH3+). For example, pKaof the -NH3+group of alanine is 9.87 but the pKaof CH3NH3+is 10.63.

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

a.

b.

Devise a synthesis of the following dipeptide from amino acid starting materials.
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