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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

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

Draw the amino acids and peptide fragments formed when the decapeptide A-P-F-L-K-W-S-G-R-G is treated with each reagent or enzyme: (a) chymotrypsin; (b) trypsin; (c) carboxypeptidase; (d)C6H5N=C=S

Explain why the pKaof the -NH3+group of an 伪-amino acid is lower than the pKaof the ammonium ion derived from a 1鈭�amine (RNH3+). For example, thepKa of therole="math" localid="1648617659352" -NH3+ group of alanine is 9.87 but thepka ofCH3NH3+ is 10.63.

Draw the structure for each peptide:

(a) Phe鈥揂la;

(b) Gly鈥揋ln;

(c) Lys鈥揋ly;

(d) R-H

Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.

a. Val鈥揋lu

b. Gly鈥揌is鈥揕eu

c. M鈥揂鈥揟鈥揟
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