Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17, Problem 47P
Reaction of a polypeptide with carboxypeptidase A releases Met. The polypeptide undergoes partial hydrolysis to give the following peptides. What is the sequence of the polypeptide?
- 1. Ser, Lys, Trp
- 2. Gly, His, Ala
- 3. Glu, Val, Ser
- 4. Leu, Glu, Ser
- 5. Met, Ala, Gly
- 6. Ser, Lys, Val
- 7. Glu, His
- 8. Leu, Lys, Trp
- 9. Lys, Ser
- 10. Glu, His, Val
- 11. Trp, Leu, Glu
- 12. Ala, Met
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Reaction of a polypeptide with carboxypeptidase A releases Met. The polypeptide undergoes partial hydrolysis to give the following peptides. What is the sequence of the polypeptide?
1. Ser, Lys, Trp 4. Leu, Glu, Ser 7. Glu, His 10. Glu, His, Val
2. Gly, His, Ala 5. Met, Ala, Gly 8. Leu, Lys, Trp 11. Trp, Leu, Glu
3. Glu, Val, Ser 6. Ser, Lys, Val 9. Lys, Ser 12. Ala, Met
Vasopressin is a peptide hormone synthesized by the hypothalamus; in its reduced form it has the structure shown.
NH2
HS
H
H
H
H H
*H3N°
NH2
N'
SH
NH2
ОН
Vasopressin
NH
*H2N=
NH2
This structure is incorrect in that one of the amino acids is shown in the D-configuration, rather than the L-. Which one is it?
What is the amino acid sequence of this peptide?
Enter
your answer using the single letter abbretiavions for the amino acids; i.e. GPT, not Gly-Pro-Thr.
What is the net charge of this peptide at physiological pH?
ZI
IZ
ZI
IZ
ZI
Draw 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,
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
- For the tripeptide SerValMet a. What amino acid is located at the peptides N-terminal end? b. What amino acid is located at the peptides C-terminal end? c. How many peptide bonds are present? d. How many amide linkages are present?arrow_forwardOn complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one phenylalanine, and one valine residue. Partial hydrolysis gives the following fragments: Ala-Phe, Leu-Met, Val-Ala, Phe-Leu. It is known that the first amino acid in the sequence is valine and the last one is methionine. What is the complete sequence of amino acids?arrow_forwardHow many of the -amino acids shown in Table 26-1 contain aromatic rings? How many contain sulfur? How many contain alcohols? How many contain hydrocarbon side chains?arrow_forward
- A 1.00-mg sample of a pure protein yielded on hydrolysis 0.0165 mg of leucine and 0.0248 mg of isoleucine. What is the minimum possible molar mass of the protein? (MMleucine=MMisoleucine=131g/mol)arrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardWhat special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forward
- Glutathione (G-SH), one of the most common tripeptides in animals, plants, and bacteria, is a scavenger of oxidizing agents. In reacting with oxidizing agents, glutathione is converted to G-S-S-G. (a) Name the amino acids in this tripeptide. (b) What is unusual about the peptide bond formed by the N-terminal amino acid? (c) Write a balanced half-reaction for the reaction of two molecules of glutathione to form a disulfide bond. Is glutathione a biological oxidizing agent or a biological reducing agent? (d) Write a balanced equation for reaction of glutathione with molecular oxygen, O2 to form G-S-S-G and H2O. Is molecular oxygen oxidized or reduced in this process?arrow_forward22-61 Polyglutamic acid (a polypeptide chain made only of glutamic acid residues) has an a-helix conformation below pH 6.0 and a random-coil conformation above pH 6.0. What is the reason for this conformational change?arrow_forwardWhat is the major difference between a simple protein and a conjugated protein?arrow_forward
- Drawing Peptide Structures Draw the tripeptide that would result from cysteine attaching to the previous dipeptide on the acidic side.arrow_forward22-71 Which amino acid side chain is most frequently involved in denaturation by reduction?arrow_forwardThe shaded area in the following diagram shows CH₂ CH | H CO-H-N N-H-O -CH₂ C-OH-N Gly 193 H RN Covalent bond formation between a catalytic amino acid residue and the substrate during chymotrypsin catalysis. Acid-base catalysis by a catalytic residue in chymotrypsin. Oxyanion hole which stabilizes substrate binding in chymotrypsin catalysis. Oxyanion hole which stabilizes transition state in chymotrypsin catalysis. Low barrier hydrogen bond formation between the transition state and one of the catalytic residues of chymotrypsin. ?arrow_forward
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