EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 21, Problem 56P

A professor was preparing a manuscript for publication in which she reported that the p1 of the tripeptide Lys-Lys-Lys was 10.6. One of her students pointed out that there must be an error in her calculations because the pK2 of the ε-amino group of lysine is 10.8 and the p1 of the tripeptide has to be greater than any of its individual pKa values. Was the student correct?

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A professor was preparing a manuscript for publication in which she reported that the pI of the tripeptide Lys-Lys-Lys was 10.6. One of her students pointed out that there must be an error in her calculations because the pKa of the e-amino group of lysine is 10.8 and the pI of the tripeptide has to be greater than any of its individual pKa values. Was the student correct?
T11.1. A student was provided with the following compounds: (i) N-acetyl-L-Aspartic acid (ii) tert-butyl amine and (iii) coupling agent N,N'-dicyclohexylcarbodiimide (DCC) – to create peptide(s). The synthesis was successfully completed at 100% conversion, where a 2:1 ratio of the amine to amino acid was used and all possible peptide bonds were formed. If partial racemization also took place during the synthesis, how many types of product(s) can the student possibly obtain from the reaction? HO. CH, OH Ö HN. CH, H,C NH2 (A) 1 (B) 2 (C) 3 (D) 4 (E) 5 (F) 6 (G) None of these T11.2. Referring to T11.1: assuming the synthesis was successfully completed at 100% conversion ONLY to form Dipeptide(s) while partial racemization also took place, how many types of Dipeptide product(s) can the student possibly obtain from the reaction? (A) 1 (B) 2 (C) 3 (D) 4 (E) 5 (F) 6 (G) None of these
Peptides can be separated using an ion-exchange column based on their isoelectric (pI) values. At which pH values would two different peptides, one with a pl of 5.6 and the other with a pl of 8.6, bind to a cation- and anion-exchange column? Each peptide may be capable of binding to each column at more than one pH value. anion-exchange column at pH = 4.0 pH = 6.5 pH = 10.1 cation-exchange column at = 4.0 pH pH = pH = 6.5 = 10.1 Answer Bank peptide B pl = 8.6 peptide A pl = 5.6

Chapter 21 Solutions

EBK ORGANIC CHEMISTRY

Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
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