Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Question
Chapter 17, Problem 49P
Interpretation Introduction
Interpretation:
The difference in the
Concept introduction:
The value of
If the acidity or easiness of the protonation is high for a compound, then the value of the
The structure of alanine is,
The structure of serine is,
The structure of cysteine is,
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Explain why the pI of lysine is the average of the pKa values of its two protonated amino groups.
Explain the difference in the pKa values of the carboxyl groups of alanine, serine, and cysteine.
The pKa values of alpha-amino group, carboxylic acid group and the sidechain group of arginine are 9.04,
2.17 and 12,48 respectively. What percentage of arginine molecules would be neutral in a solution of arginine
at pH 13?
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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- Glycine has pKa values of 2.3 and 9.6. Do you expect the pKa values of glycylglycine to be higher or lower than these values?arrow_forward8. The following proteins represent a wide range of molecular weights and isoelectric points. Mr is the molecular weight of a single protein chain. • Protein 1: Mr 68,544; pl 6.11 (monomer) • Protein 2: Mr 29,041; pl 5.32 (dimer) • Protein 3: Mr 15,805; pl 5.7 (dimer) • Protein 4: Mr 12,165; pl 4.74 a. Which protein is the most acidic? Explain your answer. b. Which protein will migrate the slowest in an SDS-PAGE? Explain your answer. c. In what order will these proteins elute from a cation exchanger at pH 8? Explain your answer. d. In what order will these proteins salt out from a pH 7 solution by the dropwise addition of saturated ammonium sulfate? Explain your answer. 5 83°F Cloudyarrow_forwardGuanidine and the guanidino group present in arginine are two of the strongest organic bases known. Account for their basicity.arrow_forward
- Calculate the isoelectric point for each amino acid.a. cysteine: pKa (COOH) = 2.05; pKa (a-NH3+) = 10.25b. methionine: pKa (COOH) = 2.28; pKa (a-NH3+) = 9.21arrow_forwardDraw the structures of the amino acids phenylalanine and aspartate in the ionization state you would expect at pH 7.0. Why is aspartate very soluble in water, whereas phenylalanine is much less soluble?arrow_forwardHemoglobin A has a pI value of 5.6 whereas the variant hemoglobin M has an aspartate residue in place of the normal valine at position 85 of the alpha chain. What effect will this substitution have on the electrophoretic behavior of the protein at pH 7.0. (explain clearly the reason for your answer)arrow_forward
- Why are the carboxylic acid groups of the amino acids more acidic (pKa - 2) than a carboxylic acid such as acetic acid (pKa = 4.76)?arrow_forwardThe pKa of the amino and carboxyl groups on alanine are 9.9 and 2.4, respectively. Under physiological conditions (pH 7.4), what percentage of alanine is ionized?arrow_forwardThe three pKa values for this amino acid slycine are 1.9, 7.5, and 10.8. Calculate the isoelectric point of this amino acid.arrow_forward
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