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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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.
1. What test reagents are used for the alkylation of amino acids (alkylating reagents)?
2. What test reagents are used for acid hydrolyzation of amino acids
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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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
- Which of the following are true concerning the chemical bond that forms between the carboxyl (RCOOH) group of one amino acid and the amino (RCNH2) group of another? a.The bond is called a peptide bond. b.It is formed by inserting a water molecule between them. c.It is formed by a dehydration reaction. d.A polypeptide has more of these bonds than a protein.arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?arrow_forward4) What would happen if you treated Alanine (above) with an aqueous solution of: a. HCI HO b. NaOH HO NH₂ NH₂ HCI NaOHarrow_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_forwardDraw 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-Tarrow_forwardAnother method to form a peptide bond involves a two-step process:[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.[2] Reaction of the p-nitrophenyl ester with an amino acid ester.a. Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation? b. Would a p-methoxyphenyl ester perform the same function? Why or why not?arrow_forward
- Identify the individual amino acids in each dipeptide, and then name the dipeptide using three-letter abbreviations.arrow_forwardDraw structures from notations or notations from structures, for the following tripeptides. (EOCQ 62) it. For drawing the structure of a tripeptide, follow the hints given in the previous question; you will have to connect three amino acid molecules in the specified order. а. Cys-Gly-Ala b. Ser-Leu-Val Нон НОН Но С. H,N-C-C-N-Ç-C-N-C-C-OH CH,CH,CHCH, CH3 C,H,CH, НОНН онНО d. H,N-C-C-N-C-C-N-Ç-C-OH CH,SCH,CH, CH-CНОН НSCH,arrow_forward47. A pentapeptide on complete hydrolysis yields 3 moles of glycine (R=H), 1 mole of alanine (R=CH3) and 1 mole of serine (R=CH2OH). On partial hydrolysis, the fragments are ala-gly, gly-ala and gly-ser. The pentapeptide is negative to the Sanger reaction. Draw a possible structure for the pentapeptide.arrow_forward
- α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. Draw the structures of the two intermediates formed in this reaction.arrow_forwardConsider the structure of L-alanine. CH3 *H3N₁ L-alanine Which structural components are common to all amino acids? H COO™ CH3 NHarrow_forward1.Draw Fischer projection formulas for the following amino acids. L-Serine D-Serine D-Alanine L-Leucine 2. Draw the structure of alanylglutamylglycyllysinearrow_forward
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