Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17.1, Problem 1P
- a. Explain why, when the imidazole ring of histidine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton. (Hint: Localized electrons are more apt to be protonated than delocalized electrons.)
- b. Explain why, when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton.
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4) What would happen if you treated Alanine (above) with an aqueous solution of:
a. HCI
HO
b. NaOH
HO
NH₂
NH₂
HCI
NaOH
Explain why, when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton.
10. Which side chain would most likely be found in the interior of a protein, away
from the aqueous environment?
a.
-CH2OH
b. -CH2SH
с. -СH-CООН
d. -CH2CONH2
e.
Chapter 17 Solutions
Essential Organic Chemistry (3rd 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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- 1. Determine the isolation points (kasein) of alanine and argininearrow_forwardThe RGD peptide is critical for the establishment of the extracellular matrix of animal cells. a. Draw the structure of the RGD peptide at physiological pH (pH = 7). b. What is the charge of this peptide at physiological pH? At high pH (pH> 13)? Low pH (pH < 3)?arrow_forward1. structure of L-valine in a strongly basic solution. 2. What is the charge of this amino acid in a strongly basic solution? 3. What is the pH of D at its isoelectric point? 4. show the structure of this amino acid at its isoelectric point. 5. What is the charge of this amino acid in a strongly acidic solution?arrow_forward
- 1. At what pH is the side chain of arginine 65% ionized? 2. At what pH is glutamate 25% ionized? 3. At what pH is the side chain of histidine 4/5 ionized? 4. At what pH is the side chain of cysteine 15% ionized? 5. At what pH is tyrosine 5/8 ionized?arrow_forwardWhich one is Second prominent form of arginine at pH 6.0 in the picture below?arrow_forwardA. Draw the structure of L-valine in a strongly basic solution. B. What is the charge of this amino acid in a strongly basic solution? C. What is the pH of D at its isoelectric point? D. Show the structure of this amino acid at its isoelectric point. E. What is the charge of this amino acid in a strongly acidic solution?arrow_forward
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