Organic Chemistry (Loose) -With Access
7th Edition
ISBN: 9780321933805
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 22.13, Problem 40P
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
(a) Draw the structure of the two possible dipeptides that can be formed by combining valine and phenylalanine. (b) In each dipeptide, label the N- and C-terminal amino acids. (c) Name each peptide using three-letter symbols.
A decapeptide undergoes partial hydrolysis to give peptides whose amino acid compositions are shown. Reaction of the intact decapeptide with Edman’s reagent releases PTH-Gly. What is the sequence of the decapeptide? 1. Ala, Trp 3. Pro, Val 5. Trp, Ala, Arg 7. Glu, Ala, Leu
2. Val, Pro, Asp 4. Ala, Glu 6. Arg, Gly 8. Met, Pro, Leu, Glu
Chapter 22 Solutions
Organic Chemistry (Loose) -With Access
Ch. 22.1 - a. Explain why, when the imidazole ring of...Ch. 22.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 22.2 - Prob. 4PCh. 22.3 - Prob. 5PCh. 22.3 - Prob. 6PCh. 22.3 - Draw the predominant form for glutamate in a...Ch. 22.3 - a. Why is the pKa of the glutamate side chain...Ch. 22.4 - Explain why the pI of lysine is the average of the...Ch. 22.4 - Calculate the pI of each of the following amino...Ch. 22.4 - a. Which amino acid has the lowest pI value? b....
Ch. 22.4 - Prob. 13PCh. 22.5 - What aldehyde is formed when valine is treated...Ch. 22.5 - Prob. 15PCh. 22.5 - Prob. 16PCh. 22.5 - Prob. 17PCh. 22.5 - Prob. 18PCh. 22.6 - Why is excess ammonia used in the preceding...Ch. 22.6 - Prob. 20PCh. 22.6 - What amino acid is formed using the...Ch. 22.6 - Prob. 22PCh. 22.6 - What amino acid is formed when the aldehyde used...Ch. 22.7 - Esterase is an enzyme that catalyzes the...Ch. 22.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 22.8 - Prob. 26PCh. 22.8 - Prob. 27PCh. 22.8 - Which bonds in the backbone of a peptide can...Ch. 22.9 - What is the configuration about each of the...Ch. 22.9 - Glutathione is a tripeptide whose function is to...Ch. 22.10 - What dipeptides would be formed by heating a...Ch. 22.10 - Suppose you are trying to synthesize the dipeptide...Ch. 22.10 - Show the steps in the synthesis of the...Ch. 22.10 - a. Calculate the overall yield of bradykinin when...Ch. 22.11 - Show the steps in the synthesis of the...Ch. 22.13 - Prob. 36PCh. 22.13 - In determining the primary structure of insulin,...Ch. 22.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 22.13 - Explain why cyanogen bromide does not cleave on...Ch. 22.13 - Indicate the peptides produced from cleavage by...Ch. 22.13 - Prob. 42PCh. 22.13 - Three peptides were obtained from a trypsin...Ch. 22.14 - Prob. 44PCh. 22.15 - How would a protein that resides in the nonpolar...Ch. 22.16 - a. Which would have the greatest percentage of...Ch. 22 - Prob. 47PCh. 22 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Aspartame (its structure is on page 1007) has a pl...Ch. 22 - Draw the form of aspartate that predominates at...Ch. 22 - A professor was preparing a manuscript for...Ch. 22 - Prob. 54PCh. 22 - Determine the amino acid sequence of a polypeptide...Ch. 22 - Prob. 56PCh. 22 - Which is the more effective buffer at...Ch. 22 - Identify the location and type of charge on the...Ch. 22 - Draw the product obtained when a lysine side chain...Ch. 22 - After the polypeptide shown below was treated with...Ch. 22 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 22 - Show how aspartame can be synthesized using DCCD.Ch. 22 - -Amino acids can be prepared by treating an...Ch. 22 - Reaction of a polypeptide with carboxypeptidase A...Ch. 22 - a. How many different octapeptides can be made...Ch. 22 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 22 - A mixture of 15 amino acids gave the fingerprint...Ch. 22 - Write the mechanism for the reaction of an amino...Ch. 22 - Prob. 69PCh. 22 - Show how valine can be prepared by a. a...Ch. 22 - A chemist wanted to test his hypothesis that the...Ch. 22 - Propose a mechanism for the rearrangement of the...Ch. 22 - A normal polypeptide and a mutant of the...Ch. 22 - Determine the amino acid sequence of a polypeptide...
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- Deduce the amino acid sequence of an undecapeptide (11 amino acids) from the experimental results shown in the table.arrow_forwardThe octapeptide angiotensin II has the sequence Asp-Arg-Val-Tyr-Ile-His-Pro- Phe. What fragments would result if angiotensin II were cleaved with trypsin? With chymotrypsin?arrow_forwardA peptide has the following amino acid composition: 2 Met, 2 Phe, 2 Glu, 1 Arg, 1 Lys, 1 Val, 1 Leu, 1 Gly, 1 Ser Reaction of the intact peptide with dansyl chloride followed by acid hydrolysis creates a derivative of Met. A specific cleavage of the intact peptide produces fragments with the following sequences: Fragment A: Glu-Gly-Lys-Phe Fragment B: Met-Ser-Leu-Arg Fragment C: Met-Val-Glu-Phe What information do this result give about the sequence of the peptide? Explain how you arrived on your answer. a) The sequence is: Met-Val-Glu-Phe-Glu-Gly-Lys-Phe-Met-Ser-Leu-Arg b) The sequence is: Met-Ser-Leu-Arg-Met-Val-Glu-Phe-Glu-Gly-Lys-Phe c) The sequence is: Met-Val-Glu-Phe-Met-Ser-Leu-Arg-Glu-Gly-Lys-Phe d) The sequence is: Met-Ser-Leu-Arg-Glu-Gly-Lys-Phe-Met Val-Glu-Phearrow_forward
- Report the isoelectric point of the peptide, Gly-Asp-Lys-Ile?arrow_forwardA tetrapeptide is given as: Ser-Lys-Ala-Phe. Which statement is true? a. The listing should be in alphabetical order. b. There are four peptide bonds because there are four amino acids. c. The serine provided a nitrogen for the peptide bond. d. The N-terminus is serine (Ser).arrow_forwardConsider the pentapeptide Ile-Lys-Asp-Phe-Gly and answer the following (use the pKa values in the table): 1. Draw the structure of the predominant form of the pentapeptide at pH = 12. 2. Draw the structure of the Zwitterion form of the pentapeptide. 3. What is the IpH of the peptide?arrow_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_forwardWhich of the following peptides have a net positive chargeat pH 7? (a) Gly-Ser-Lys, (b) Pro-Leu-Ile, (c) Phe-Tyr-Asp.arrow_forward
- His-Met-Asp-Tyr-Phe-Ser within this peptide, which amino acid residue is the most hydrophobic and why?arrow_forwardAnother method to form a peptide bond involves a two-step process Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forwardThe peptide cys-leu-glu-ala-cys-lys is at pH 7 in oxidizing conditions. Part a) Draw the peptide's structure. Circle the C-terminus and box the N-terminus. Part b) Draw a titration curve for the peptide. Part c) If the peptide is at pH 2, what would be the total charge?arrow_forward
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