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Chapter 29: 21P (page 1172)

(a) What products are formed when each peptide is treated with trypsin? (b) What products are formed when each peptide is treated with chymotrypsin?

[1] Gly鈥揂la鈥揚he鈥揕eu鈥揕ys鈥揂la

[2] Phe鈥揟yr鈥揋ly鈥揅ys鈥揂rg鈥揝er

[3] Thr鈥揚ro鈥揕ys鈥揋lu鈥揌is鈥揋ly鈥揚he鈥揅ys鈥揟rp鈥揤al鈥揤al鈥揚he

Short Answer

Expert verified

Cleavage by Trypsin:

[1] Gly鈥揂la鈥揚he鈥揕eu鈥揕ys + Ala

[2] Phe鈥揟yr鈥揋ly鈥揅ys鈥揂rg + Ser

[3] Thr鈥揚ro鈥揕ys + Glu鈥揌is鈥揋ly鈥揚he鈥揅ys鈥揟rp鈥揤al鈥揤al鈥揚he

Cleavage by Chymotrypsin

[1] Gly鈥揂la鈥揚he + Leu鈥揕ys鈥揂la

[2] Phe + Tyr + Gly鈥揅ys鈥揂rg鈥揝er

[3] Thr鈥揚ro鈥揕ys鈥揋lu鈥揌is鈥揋ly鈥揚he + Cys鈥揟rp + Val鈥揤al鈥揚he

Step by step solution

01

Hydrolysis of peptides by enzymes

The peptide bonds can be hydrolyzed at specific sites by the enzymes like trypsin, chymotrypsin, and carboxypeptidase.

02

Cleavage by Trypsin

Trypsin catalyzes the hydrolysis of amides with a carbonyl group that is part of the basic amino acids arginine and lysine.

[1] Gly鈥揂la鈥揚he鈥揕eu鈥揕ys + Ala

[2] Phe鈥揟yr鈥揋ly鈥揅ys鈥揂rg + Ser

[3] Thr鈥揚ro鈥揕ys + Glu鈥揌is鈥揋ly鈥揚he鈥揅ys鈥揟rp鈥揤al鈥揤al鈥揚he

03

Cleavage by Chymotrypsin

Chymotrypsin hydrolyzes amides with carbonyl group that is part of the aromatic amino acids phenylalanine, tyrosine, and tryptophan.

[1] Gly鈥揂la鈥揚he + Leu鈥揕ys鈥揂la

[2] Phe + Tyr + Gly鈥揅ys鈥揂rg鈥揝er

[3] Thr鈥揚ro鈥揕ys鈥揋lu鈥揌is鈥揋ly鈥揚he + Cys鈥揟rp + Val鈥揤al鈥揚he

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Most popular questions from this chapter

Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly鈥揂la鈥揝er and Ala鈥揝er鈥揂rg

Give the amino acid sequence of each peptide using the fragments obtained by partial hydrolysis of the peptide with acid.

  1. A tetrapeptide that contains Ala, Gly, His, and Tyr, which is hydrolyzed to the dipeptides His-Tyr, Gly-Ala, and Ala-His.
  2. A pentapeptide that contains Glu, Gly, His, Lys, and Phe, which is hydrolyzed to His-Gly-Glu, Gly-Glu-Phe, and Lys-His.

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

An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glue (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile-Leu in addition to other products. Deduce the structure of the octapeptide and fragments A-D.

Give the amino acid sequence of an octapeptide that contains the amino acids Tyr, Ala, Leu (2 equiv), Cys, Gly, Glu and Val, and forms the following fragments when partially hydrolyzed with HCl: Val-Cys-Gly-Glu, Ala-Leu-Tyr, and Tyr-Leu-Val-Cys.
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