Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 17, Problem 54P
Determine the amino acid sequence of a polypeptide from the following data: Complete hydrolysis of the peptide yields Ala, Arg, Gly, 2 Lys, Met, Phe, Pro, 2 Ser, Tyr, and Val. Treatment with Edman’s reagent releases PTH-Val.
Carboxypeptidase A releases Ala.
Treatment with cyanogen bromide yields the following two peptides:
- 1. Ala, 2 Lys, Phe, Pro, Ser, Tyr
- 2. Arg, Gly, Met, Ser, Val
Treatment with trypsin yields the following three peptides:
- 1. Gly, Lys, Met, Tyr
- 2. Ala, Lys, Phe, Pro, Ser
- 3. Arg, Ser, Val
Treatment with chymotrypsin yields the following three peptides:
- 1. 2 Lys, Phe, Pro
- 2. Arg, Gly, Met, Ser, Tyr, Val
- 3. Ala, Ser
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Give the amino acid sequence of each peptide using the fragments obtained by partial hydrolysis of the peptide with acid.
a. a tetrapeptide that contains Ala, Gly, His, and Tyr, which is hydrolyzed to the dipeptides His-Tyr, Gly-Ala, and Ala-His
b. a pentapeptide that contains Glu, Gly, His, Lys, and Phe, which is hydrolyzed to His-Gly-Glu, Gly-Glu-Phe, and Lys-His
Hydrolysis of decapeptide P with the enzyme trypsin affords the following fragments: Gly-Asp, Ala-Cys-Lys, Leu-Trp-
Val-Gly-Arg.
Hydrolysis with chymotrypsin yields: Leu-Trp, Val-Gly-Arg-Ala-Cys-Lys-Gly-Asp.
What is the amino acid sequence of P?
A decapeptide has the following amino acid composition:Ala2 , Arg, Cys, Glu, Gly, Leu, Lys, Phe, ValPartial hydrolysis yields the following tripeptides:Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala+ Lys-Val-Phe + Val-Phe-Gly.Reaction of the decapeptide with 2,4-dinitrofluorobenzene yields 2,4-dinitrophenylysine.
Fromthe experimental data, suggest a scheme you will follow to synthesize the dipeptide Ala-Gly
Chapter 17 Solutions
Essential Organic Chemistry, Global Edition
Ch. 17.1 - a. Explain why, when the imidazole ring of...Ch. 17.2 - Prob. 2PCh. 17.3 - Prob. 3PCh. 17.3 - Prob. 4PCh. 17.3 - Prob. 6PCh. 17.4 - Calculate the pI of each of the following amino...Ch. 17.4 - a. Which amino acid has the lowest pI value? b....Ch. 17.5 - What aldehyde is formed when valine is treated...Ch. 17.5 - Prob. 10PCh. 17.5 - Prob. 11P
Ch. 17.5 - Prob. 12PCh. 17.6 - Prob. 13PCh. 17.6 - What amino acid would be formed using the...Ch. 17.6 - What amino acid would be formed when the aldehyde...Ch. 17.7 - Pig liver esterase is an enzyme that catalyzes the...Ch. 17.8 - Prob. 17PCh. 17.8 - Prob. 18PCh. 17.8 - Prob. 19PCh. 17.8 - Prob. 20PCh. 17.10 - Prob. 21PCh. 17.10 - Prob. 22PCh. 17.10 - Why does cyanogen bromide not cleave on the C-side...Ch. 17.10 - Prob. 24PCh. 17.10 - Prob. 26PCh. 17.12 - Prob. 27PCh. 17.13 - a. Which would have the greatest percentage of...Ch. 17 - Draw the predominant form of the following amino...Ch. 17 - What is the pI of serine?Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Which would have a higher percentage of negative...Ch. 17 - Draw the form of aspartate that predominates at...Ch. 17 - Prob. 35PCh. 17 - A professor was preparing a manuscript for...Ch. 17 - a. Why is the pKa of the glutamate side chain...Ch. 17 - Prob. 38PCh. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Three peptides were obtained from a trypsin...Ch. 17 - Prob. 43PCh. 17 - After the polypeptide shown here was treated with...Ch. 17 - The disulfide bridges of a polypeptide were...Ch. 17 - -Amino acids can be prepared by treating an...Ch. 17 - Reaction of a polypeptide with carboxypeptidase A...Ch. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Show how valine can be prepared by a. a Strecker...Ch. 17 - Prob. 51PCh. 17 - Why is proline never found in an -helix?Ch. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 55PCh. 17 - A chemist wanted to test his hypothesis that the...Ch. 17 - A normal polypeptide and a mutant of the...
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