Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 17, Problem 46P
α-Amino acids can be prepared by treating an
a. Draw the structures of the two intermediates formed in this reaction.
b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?
c. What aldehyde would be needed to prepare isoleucine?
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Which amino acids on proteins can form glycosidic linkages?
Select one:
a. Cysteine and methionine
b. Tryptophan and phenylalanine
c. Glycine and proline
d. Serine and asparagine
e. Alanine and leucine
alpha-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. a. Draw the structures of the two intermediates formed in this reaction. b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal? c. What aldehyde is needed to prepare isoleucine?
Draw the structure of a naturally occurring amino acid that is a neutral amino acid with a phenol in its side chain.
Chapter 17 Solutions
Essential Organic Chemistry, Global 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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- Please answer these 3 questions below. 1. What type of interaction would you expect between the R groups, lysine and aspartic acid, in tertiary structure? a. Hydrophilic b. Disulfide bonds c. Hydrophobic/London dispersion d. Electrostatic interactions e. Hydrogen bond 2. Which of the following amino acids have R groups that are polar? Cystine, Glutamine, Leucine a. Cysteine, Glutamine, Leucine are all polar b. Only Cysteine and Glutamine are polar c. Only Glutamine and Leucine are polar d. Only Leucine is polar e. None of the listed amino acids are polararrow_forwardIdentify the major class of each lipid from its components. a. fatty acids + glycerol b. fatty acids + sphingosine + a carbohydrate c. fatty acids + high-molecular-weight alcohols other than glycerol d. glycerol + fatty acids + phosphate group + choline e. fatty acids + sphingosine + phosphate group + a nitrogen compoundarrow_forward10. Consider the amino acids glycine, valine and lysine. a. How many tripeptides can be formed from these three amino acids if each is used only once in the structure? b. Using three-letter abbreviations for the amino acids, give the sequence of each of the possible tripeptides. c. Draw the structure of the dipeptide that has valine at its N-terminal amino acid and glycine as its C-terminal amino acid. Circle each peptide bond.arrow_forward
- 3. Write the formulas of alanine and the products obtained from it when it is oxidized by ninhydrin. Which product reacts with ninhydrin to form a colored substance.arrow_forward1. Secondary structures of proteins are held together by hydrogen bonding Select one: a. from one a-amino groups of the protein backbone to another a-amino group of the protein backbone. b. between a-amino groups and carbonyl groups of the protein backbone. c. from one carbonyl group of the protein backbone to another carbonyl group of the protein backbone. d. between side chain R groups. 2. What is the primary organic product of oxidation of the following molecule? Select one: a. 4-methyl-2-hexanone b. 4-methyl-2-hexanal C. 4-methyl-2-hexanoic acid d. No reactionarrow_forward39. 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_forward
- Explain why amino acids, unlike most other organic compounds, are insoluble in organic solvents like diethyl ether.arrow_forwardA protein has a tertiary structure formed by interactions between the side chains of the following pairs of amino acids. For each pair, identify the strongest type of interaction between these amino acids. a. Valine and isoleucine b. Asparagine and serine c. Glutamic acid and arginine d. Tryptophan and methionine Write the products for the complete hydrolysis of: NH2 NH NH HO H2N но Nextarrow_forwardThe carbonyl group on D-glucose can be reduced to d-glucitol. Identify the reagents that can chrry out this reduction. A.water in acidic solution B. hydrogen with a Platinum catalyst (Hy/Pt) C. Sodium dichromate (NaCr2O) in acidic solution D. Benedict’s reagent E. Enzymesarrow_forward
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