Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 22.3, Problem 9P
- a. Why is the pKa of the glutamate side chain greater than the pKa, of the aspartate side chain?
- b. Why is the pKa of the arginine side chain greater than the pKa of the lysine side chain?
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Why is the side chain Pka of amino acid so much higher ?
Why is the pKa of the arginine side chain greater than the pKa of the lysine side chain?
Why is the pKa of the glutamate side chain greater than the pKa of the aspartate side chain?
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - a. Explain why, when the imidazole ring of...Ch. 22.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 22.2 - Prob. 4PCh. 22.3 - Prob. 5PCh. 22.3 - Prob. 6PCh. 22.3 - Draw the predominant form for glutamate in a...Ch. 22.3 - a. Why is the pKa of the glutamate side chain...Ch. 22.4 - Explain why the pI of lysine is the average of the...Ch. 22.4 - Calculate the pI of each of the following amino...Ch. 22.4 - a. Which amino acid has the lowest pI value? b....
Ch. 22.4 - Prob. 13PCh. 22.5 - What aldehyde is formed when valine is treated...Ch. 22.5 - Prob. 15PCh. 22.5 - Prob. 16PCh. 22.5 - Prob. 17PCh. 22.5 - Prob. 18PCh. 22.6 - Why is excess ammonia used in the preceding...Ch. 22.6 - Prob. 20PCh. 22.6 - What amino acid is formed using the...Ch. 22.6 - Prob. 22PCh. 22.6 - What amino acid is formed when the aldehyde used...Ch. 22.7 - Esterase is an enzyme that catalyzes the...Ch. 22.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 22.8 - Prob. 26PCh. 22.8 - Prob. 27PCh. 22.8 - Which bonds in the backbone of a peptide can...Ch. 22.9 - What is the configuration about each of the...Ch. 22.9 - Glutathione is a tripeptide whose function is to...Ch. 22.10 - What dipeptides would be formed by heating a...Ch. 22.10 - Suppose you are trying to synthesize the dipeptide...Ch. 22.10 - Show the steps in the synthesis of the...Ch. 22.10 - a. Calculate the overall yield of bradykinin when...Ch. 22.11 - Show the steps in the synthesis of the...Ch. 22.13 - Prob. 36PCh. 22.13 - In determining the primary structure of insulin,...Ch. 22.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 22.13 - Explain why cyanogen bromide does not cleave on...Ch. 22.13 - Indicate the peptides produced from cleavage by...Ch. 22.13 - Prob. 42PCh. 22.13 - Three peptides were obtained from a trypsin...Ch. 22.14 - Prob. 44PCh. 22.15 - How would a protein that resides in the nonpolar...Ch. 22.16 - a. Which would have the greatest percentage of...Ch. 22 - Prob. 47PCh. 22 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Aspartame (its structure is on page 1007) has a pl...Ch. 22 - Draw the form of aspartate that predominates at...Ch. 22 - A professor was preparing a manuscript for...Ch. 22 - Prob. 54PCh. 22 - Determine the amino acid sequence of a polypeptide...Ch. 22 - Prob. 56PCh. 22 - Which is the more effective buffer at...Ch. 22 - Identify the location and type of charge on the...Ch. 22 - Draw the product obtained when a lysine side chain...Ch. 22 - After the polypeptide shown below was treated with...Ch. 22 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 22 - Show how aspartame can be synthesized using DCCD.Ch. 22 - -Amino acids can be prepared by treating an...Ch. 22 - Reaction of a polypeptide with carboxypeptidase A...Ch. 22 - a. How many different octapeptides can be made...Ch. 22 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 22 - A mixture of 15 amino acids gave the fingerprint...Ch. 22 - Write the mechanism for the reaction of an amino...Ch. 22 - Prob. 69PCh. 22 - Show how valine can be prepared by a. a...Ch. 22 - A chemist wanted to test his hypothesis that the...Ch. 22 - Propose a mechanism for the rearrangement of the...Ch. 22 - A normal polypeptide and a mutant of the...Ch. 22 - Determine the amino acid sequence of a polypeptide...
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- Why is the pK a of the glutamate side chain greater than the pKa of the aspartate side chain?arrow_forwardArginine has these pKa values: pka1 for the carboxyl group = 2.17, pKa2 for the amino group = 9.04, and pKaR for the side chain - 12.48 At pH 7, which groups in arginine are protonated? amino and side chain O B. none Oç all OD. carboxyl and side chain side chain only OE.arrow_forwardLectin 1 Lectin receptor 2 Asialo glycoprotein receptor 3 P Selectin 4 5 6 Ricin 7 Concanavalin A 8 Glycophorin Hemagglutinin H. pylori lectin Saccharide Affinity Location Biol. Functionarrow_forward
- 3. Pepsin cleavage of the peptide Ala-His-Gly-Trp-Val-lle-Arg-Gly would yield the peptides Ala-His-Gly-Trp and Val-Ile-Arg-Gly. 4. Argininosuccinate synthetase converts citrulline and aspartate into argininosuccinate. T F T Farrow_forwardWould a lipase hydrolyze two triglycerides, one containing only oleic acid and the other containing only palmitic acid, with equal ease?arrow_forwardArginine exists in two high-pH forms instead of the usual one. Explain why.arrow_forward
- 0 Can the product of a reaction that is part of a sequence act as an inhibitor for another reaction in the sequence? Explain.arrow_forwardIf the pH of a solution of Arginine is equal to a half of the 3 pka values of all of its functional groups, what will be the charge on the majority of the Arg molecules in that solution? Please explain. Am i supposedd to add up the three pka values and then divide it in half to find the pH? Thanksarrow_forward23. Rank the following molecules in the increasing order of their pka A. IKIIKKIV B. IIK<arrow_forward1. 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_forwardWhat is the type of inhibitor if both Vmax and Km are increased? (Provide an explanation/justification to the selected answer) a. Competitive inhibitor b. Non-competitive inhibitor c. Uncompetitive inhibitorarrow_forwardYou are called in as a consult for a patient who suffers from acidosis. Urine levels of both lactic acid and isocitric acid are elevated. Mitochondria isolated from the patient’s fibroblasts oxidize pyruvate very slowly whereas α-ketoglutarate and malate are oxidized normally. a. At what enzyme would you predict the patient has a defect? b. Why? What evidence do you have to choose that enzyme? c. How do you account for the increase in lactic acid?arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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