Concept explainers
An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxy peptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides,
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Chapter 27 Solutions
ORGANIC CHEMISTRY
- For the tripeptide GlyAlaCys 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_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forwardFor 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
- 22-47 How many different tetrapeptides can be made (a) if the peptides contain the residues of asparagine, proline, serine, and metbionine and (b) if all 20 amino acids can be used?arrow_forwardA 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_forwardAspartame (Nutrasweet®) is a remarkably sweet-tasting dipeptide ester. Complete hydrolysis of aspartame gives phenylalanine, aspartic acid, and methanol. Mild incubation with carboxypeptidase has no effect on aspartame. Treatment ofaspartame with phenyl isothiocyanate, followed by mild hydrolysis, gives the phenylthiohydantoin of aspartic acid.Propose a structure for aspartame.arrow_forward
- The structure of the artificial sweetener aspartame is shown below. What type of linkage is found in this compound? H. +H,N-CH-C-N-CH C-OCH, CH2 CH2 C3D0 Aspartame (Asp-Phe-OMe) O peptide bond O phosphoester linkage O ester linkage O glycosidic linkagearrow_forwardProline is the only naturally occurring amino acids that can exist in two conformational states referred to as cis and trans proline when incorporated into peptides. a) Draw the cis and trans conformations of the proline containing tripeptide NH(Fmoc)-Val-Pro- Trp-COОH b) In most cases the trans proline amid conformation is preferred. Design two proline mimetics that allow to populate preferably the cis amide rotamer conformation of proline in tripeptide NH(Fmoc)-Val-Pro-Trp-COOH c) Outline strategies that can be used to populate the cis amide state of other amino acids. Use the amino acid ornithine as an examplearrow_forward5.Indicate the amino acid as polar or nonpolar OH CH: 0 H₂N-C-C-OH H O CH, 0 !! H₂N-C-C-o H CH3 CH3 CH CHO 11₂N-C-C-07 H 6) Acids and bases denature a protein by disrupting A) peptide bonds and ionic bonds. B) amide bonds and alkene bonds. C) hydrophobic interactions and peptide bonds. D) ionic bonds and hydrophobic interactions. E) ionic bonds and hydrogen bonds. 5) Heat denatures a protein by disrupting A) ionic bonds and peptide bonds. B) hydrophobic bonds and hydrogen bonds. C) peptide bonds and hydrophobic bonds. D) disulfide bonds and peptide bonds. E) hydrogen bonds and disulfide bonds. 7) Denaturation of a protein A) changes the primary structure of a protein. B) disrupts the secondary, tertiary, or quaternary structure of a protein. C) is always irreversible. D) hydrolyzes peptide bonds. E) can only occur in a protein with quaternary structure. 8) Heavy metals denature proteins by A) releasing amino acids. B) disrupting hydrophobic interactions. C) changing the pH of the…arrow_forward
- Treating chitin with H2O, -OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, bers for sutures, and wound dressings.arrow_forwardO2CCH,CH,-C-CO2 + CH2 NH3 NH3 O2CCH,CH,-C-CO2 + CH2 CH2-C-CO2 + H. phenylalanine -CO2 0,CCH,CH2—CO2 CH2-C-CO2arrow_forwardPlease explain the answer in detailsarrow_forward
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