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ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 21.8, Problem 27P
Draw the resonance contributors of the peptide bond in the less stable configuration.
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Lysine and tryptophan are two amino acids that contain an additional Natom in the R group bonded to the a carbon. While lysine is classified asa basic amino acid because it contains an additional basic N atom,tryptophan is classified as a neutral amino acid. Explain why thisdifference in classification occurs.
If anisole is allowed to sit in D2O that contains a small amount of D2SO4, what products are formed?
Label the bond that cyclizes this peptide and note what type of covalent bond this is and what chemical groups this bond links.
Chapter 21 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- (a) Label all the O atoms that are part of a glycoside in rebaudioside A. Rebaudioside A, marketed under the trade name Truvia, is a sweet glycoside obtained from the stevia plant, which has been used for centuries in Paraguay to sweeten foods. (b) The alcohol or phenol formed from the hydrolysis of a glycoside is called an aglycon. What aglycon and monosaccharides are formed by the hydrolysis of rebaudioside A?arrow_forwardDraw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.arrow_forwarddoes structure E(attached) represent fructopyranose. explainarrow_forward
- Be sure to answer all parts. Consider the disaccharide sophorose. 7 OH OH 1 CH₂OH 0 sophorose 0. 3 ОН Н ОН 15 ОН What monosaccharides are formed when sophorose is hydrolyzed? . . draw structure ... Upper Saccharide H 10 н -I0-I 12 CH2OH IO-I Н OH Н О 00 I 6 Н Iarrow_forwardThe hydrolysis of an ester can be sped up by both acidic and basic conditions. Aminolysis of an ester can be sped up by acidic conditions, but not by basic conditions. Explain why.arrow_forwardLysine and tryptophan are two amino acids that contain an additional N atom in the R group bonded to the a carbon. While lysine is classified as a basic amino acid because it contains an additional basic N atom, tryptophan is classified as a neutral amino acid. Explain why this difference in classification occurs.arrow_forward
- why are peptide amide bonds exist either as s-cis or s-trans conformation? A) Both conformations have the large groups anti to each other B) There is partial double bond character between C and N. C) There is H-bonding between O and N. D) The side chains does not affect the conformation E) None of the abovearrow_forwardDraw Fisher projections representing the D and L forms of the following: a.aspartate b.phenylalaninearrow_forwardDraw three-dimensional representations of the following amino acids.(a) l-phenylalaninearrow_forward
- 3. The molecule to the right is: A. Cys-His with a trans peptide bond B. Cys-Pro with a trans peptide bond C. Pro-Cys with a trans peptide bond D. Pro-Cys with a cis peptide bond E. Cys-Pro with a cis peptide bond H₂N SH -COOHarrow_forwarda) Draw Haworth projections of both - and -anomers of D-fructose. Indicate which carbon is the anomeric carbon.b) Sucrose is a disaccharide made up of a molecule of D-fructose and D-glucose. Draw the structure of sucrose clearly indicating the linkage between the two monosaccharides and its biological significance.c) Tollen’s reagent is a very mild oxidizing agent which normally oxidize aldehydes but not ketones. However, both glucose and fructose give positive results with Tollen’s reagent and are classified as reducing sugars. Explain how fructose can also give positive results with Tollen’s reagent (illustrate using structures).arrow_forwardIf a protein were subjected to an acidic solution, which interactions will be disrupted?arrow_forward
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