Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 21, Problem 75P
Show how valine can be prepared by
a. a Hell-Volhard-Zelinski reaction.
b. a Strecker synthesis.
c. a reductive animation.
d. a N-phthalimidomalonic ester synthesis.
e. an acetamidomalonic ester synthesis.
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A. Draw the structure of L-valine in astrongly basic
solution.
B. What is the charge of this amino
acid in a strongly basic solution?
Disulfide linkages:
A.
are covalent bonds.
B.
are a type of electrostatic interaction.
C.
occur between methionine residues.
D.
can be disrupted by SDS.
E.
can only occur within the same polypeptide chain.
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.
a. Val–Glu
b. Gly–His–Leu
c. M–A–T–T
Chapter 21 Solutions
Organic Chemistry (8th Edition)
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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- 39. Which of the following amino acids has a sulfur-containing side chain? a. serine b. cysteine c. lysine d. methionine e. both b and d 40. Which of the following reagents can be used to cleave a tert-butoxycarbonyl (Boc) protecting group from a peptide? a. H₂/Pd b. CF3CO₂H c. Na2CO3, H₂O d. LiAlH4arrow_forwardAmong these protein assays, which work in acidic conditions? a. Biuret assay b. Bicinchoninic acid assay c. Bradford assay d. Lowry assayarrow_forwardC. Aminolysis: Anilide Formation Sample Color of precipitate formed Acetyl chloride Acetic anhydridearrow_forward
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- a. State three factors that cause the uncatalyzed hydrolysis of an ester to be a slow reaction.b. Which is faster, the hydrolysis of an ester or the aminolysis of the same ester? Explain.arrow_forwardChemistry 1. Fill in the blanks with the appropriate word or words: B-Lactam acts by inhibition They are also liberating and thus exert their rapid bactericidal effect. 2. Which sentence is correct and which is incorrect? If it is incorrect, write the correct sentence a. ß - Lactams cause transpeptidation in glycopeptides. b. ß-lactams act in the third stage of murein complex synthesis. c. ß-lactams inhibit protein synthesis in bacteria. d. Bacitracin prevents the dephosphorylation of the carrier molecule of the peptidoglycan subunit. e. Cycloserine is involved in the second stage of peptidoglycan synthesis.arrow_forward1. Type of bond a. H-bond b. Electrostatic interaction c. Hydrophobic bond d. Disulfide bond e. Peptide bond 2. Level of protein structure a. primary b. secondary c. tertiary d. quaternary 3. Method/s of denaturation. choose all that applies a. Heating to 100 degrees Celsius b. Addition of nitric acid c. Reaching Isoelectric point d. Addition of mercuric chloride e. Addition of sulphosalicylic acid f. Addition of alcohol g. Addition of ammonium sulfatearrow_forward
- the other more formal name for alpha-ketoglutarate is: Select one: a. alpha-ketobutanedioic acid b. butanedioic acid c. 2-hydroxybutanedioic acid d. 2-hydroxypropane-1,2,3-tricarboxylic acid e. alpha-ketopentanedioic acid f. but-2-enedioic acid g. 1-hydroxypropane-1,2,3-tricarboxylic acidarrow_forwardChemistry Reduced glutathione (GSH) is used to Select one a.maintain amino acid transport across cell membranes b.maintain lipid peroxidation while GSH itself is convened to oxidized glutathione (GSSG) c.maintain high level of NADPH in the cell d.reduce disulfide bonds and lipid peroxides back to their original native states while GSH is to ( GSSG)arrow_forwardb. glycosphingolipid. c. sphingomyelin. d. triacylglycerol. e. fatty acid. Free Response 24. Label the acid, the base, the conjugate acid and the conjugate base in the acid-base reaction between dopamine and water? H + H20 25. What is the pH of a solution with a [H3O*] of 12.3 x 10-9 M?arrow_forward
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