EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 21.13, Problem 41P
Indicate the peptides produced from cleavage by the indicated reagent:
- a. His-Lys-Leu-Val-Glu-Pro-Arg-Ala-Gly-Ala by trypsin
- b. Leu-Gly-Ser-Met-Phe-Pro-Tyr-Gly-Val by chymotrypsin
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Indicate the peptides produced from cleavage by the indicated reagent:
a. His-Lys-Leu-Val-Glu-Pro-Arg-Ala-Gly-Ala by trypsin
b. Leu-Gly-Ser-Met-Phe-Pro-Tyr-Gly-Val by chymotrypsin
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The peptide KNYPEH N-terminal amino group has a pKa of 8.6 and the C-terminal carboxylate group has a pKa of 4.5. What is the net charge of this peptide at a pH of 1?
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The peptide KNYPEH N-terminal amino group has a pKa of 8.6 and the C-terminal carboxylate group has a pKa of 4.5. What is the net charge of this peptide at a pH of 7?
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The peptide KNYPEH N-terminal amino group has a pKa of 8.6 and the C-terminal carboxylate group has a pKa of 4.5. What is the net charge of this peptide at a pH of 15?
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The peptide KNYPEH N-terminal amino group has a pKa of 8.6 and the C-terminal carboxylate group has a pKa of 4.5. What is the isoelectric point of this peptide?
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DU
A decapeptide has the following amino acid composition.
Ala2, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val
Partial hydrolysis yields the following tripeptides.
Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly
One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
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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- 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_forward*One of the following PePtide fragments was treated with Cyanogen bromide reagent: A) Val - Lue - Trp B)Gly-Ag-Phe-lys C) Thr-Ala-Val -Arg d) Asn-Tyr-Gin-Metarrow_forwardVasopressin 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 ZIarrow_forward
- Cleavage of the following peptide with cyanogen bromide would result in the production of smaller peptides, whereas cleavage with trypsin would result in the production of Ala-Lys-Met-Glu-Asp-Cys-Ile-Phe-Met-Cys-Trp-Glu three, three one, two two, two three, twoarrow_forwardWhat fragments are produced when the peptide shown below is treated with trypsin? Gly-Arg-Val-Phe -Leu-Lys-Met-Trp-Pro-Tyr-Cys-Serarrow_forwardConsider the heptapeptide: ser-lys-met-leu-gly-tyr-asnarrow_forward
- C. AMINO ACIDS AND PEPTIDES Consider the structure of the peptide, Asn-Gln-Gly-Ala. H₂N. OH Asn-Gln-Gly-Ala NH₂ 1. How many peptide bonds are present? 2. What is the N-terminal amino acid? Provide the three-letter name. 3. What is the C-terminal amino acid? Provide the three-letter name. H₂N,arrow_forwardHis-Met-Asp-Tyr-Phe-Ser Calculate an approximate pI (isoelectric point) for this peptide.arrow_forwardPredict the products P and Q formed when the following peptide is treated with the given reagient. HS. H₂N (b) (c) (d) HS P P OH H₂N. PhNCS DIPEA H₂N. X DH P + Q OH CHarrow_forward
- After the polypeptide shown below was treated with maleic anhydride, it was hydrolyzed by trypsin. (After a polypeptide is treated with maleic anhy-dride, trypsin will cleave the polypeptide only on the C-side of arginine.) Gly-Ala-Asp-Ala-Leu-Pro-Gly-Ile-Leu-Val-Arg-Asp-Val-Gly-Lys-Val-Glu-Val-Phe-Glu-Ala-Gly-Arg-Ala-Glu-Phe-Lys-Glu-Pro-Arg-Leu-Val-Met-Lys-Val-Glu-Gly-Arg-Pro-Val-Gly-Ala-Gly-Leu-Trparrow_forwardIn a paragraph form provide the experimental procedure of the reaction of oxazetidine-containing peptides and α-ketoacid that will result in protein that contain native serine residuesarrow_forwardQuestion 5 Which of the following are TRUE about the following peptide at pH 7? Leu-Met-Gly-Cys-Lys i. it contains 5 peptide bonds ii. it contains 5 residues iii. it absorbs maximally at 280nm iv. it has two positive charges v. it has a disulfide bond none of these O i, ii, v O i, i, ii, iv i, ii, iii, iv and v ii and ivarrow_forward
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