(a)
To determine: The structure for glutathione that is consistent with the given information and the reason corresponding to the fact that glutathione fails to give a normal product from Edmann degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis.
Interpretation: The structure for glutathione that is consistent with the given information is to be shown and the reason corresponding to the fact that glutathione fails to give a normal product from Edmann degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis is to be stated.
Concept introduction: The process in which a proper series of amino acids is maintained peptide chain is known as Edmann degradation. This process includes the labelling of terminal amino residue followed by the cleavage of this terminal amino residue from the peptide chain. The peptide bonds between other amino acids do not get disturb during this process.
(b)
To determine: The structure for glutathione disulphide that is formed by oxidation of glutathione and the balanced r-equation for the reaction of glutathione with hydrogen peroxide.
Interpretation: The structure for glutathione disulphide that is formed by oxidation of glutathione and the balanced equation for the reaction of glutathione with hydrogen peroxide are to be predicted.
Concept introduction: The process in which a proper series of amino acids is maintained peptide chain is known as Edmann degradation. This process includes the labelling of terminal amino residue followed by the cleavage of this terminal amino residue from the peptide chain. The peptide bonds between other amino acids do not get disturb during this process.
Want to see the full answer?
Check out a sample textbook solutionChapter 24 Solutions
Organic Chemistry (9th Edition)
- Cholic acid is secreted in bile as an amide linked to the aminogroup of glycine. This cholic acid–amino acid combination acts asan emulsifying agent to disperse lipids in the intestines for easierdigestion. Draw the structure of the cholic acid–glycine combination,and explain why it is a good emulsifying agent.arrow_forwardEsterase is an enzyme that catalyzes the hydrolysis of esters. It hydrolyzes esters of L-amino acids more rapidly than esters of d-amino acids. How can this enzyme be used to separate a racemic mixture of amino acids?arrow_forwardTetrapeptide A is completely hydrolysed under acidic conditions to yield alanine, aspartic acid, isoleucine and valine. On neutralisation of the hydrolysate, an odour of ammonia is detected. The reaction of the tetrapeptide with phenylisothiocyanate, followed by mild hydrolysis yields no phenylthiohydantoin derivative. Incubation of A with carboxypeptidase A has no effect either. Explain...arrow_forward
- 1. Biogenic Amines are inactivated primarily by a. Sulfonation b. Glucoronidation c. Aromatic hydroxylation d. Methylation 2. A drug can exert its pharmacological effect only if it is a. Protein bound b. Protein unbound c. Free drug d. Both B & C e. Both A & C 3. In order for the drug to be ready and available for absorption, it must be release first from its dosage form with the exception of: a. Capsule b. Tablet c. Solution d. Suspension 4. All of the following are true, except a. Solubility increase with decrease particle size b. Solubility increase with increase surface area c. Solubility increase with increase particle size d. Solubility decrease with decrease surface area 5. The rate in which the drug appears in the bloodstream is also known as a. Half-life b. Potency c. Bioavailability d. Area under the curvearrow_forwardSeveral compounds have been found to inhibit -lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the -lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements? 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different. 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group. 3. Neither the inhibitor nor the antibiotic contains strained rings. 4. Both 1 and 2 are true.arrow_forwardLeuprolide is a synthetic nonapeptide used to treat both endometriosis in women and prostate cancer in men. (a) Both C-terminal and N-terminal amino acids in leuprolide have been structurally modified. Identify the modifications. (b) One of the nine amino acids in leuprolide has d stereochemistry rather than the usual L. Which one? (c) Write the structure of leuprolide using both one- and three-letter abbreviations. (d) What charge would you expect leuprolide to have at neutral pH?arrow_forward
- Give the amino acid sequence of hexapeptides that produce the following sets of fragments upon partial acid hydrolysis: (a) Arg, Gly, Ile, Leu, Pro, Val gives Pro-Leu-Gly, Arg-Pro, Gly-Ile-Val (a) N, L, M, W, V2 gives V-L, V-M-W, W-N-Varrow_forwardAn unknown decapeptide was isolated and characterized. Complete hydrolysis of this peptide gave : F(2), A,G,C,K,N,T, W and V. Treatment with carboxypeptidase releases A. Reaction with Edman’s reagent gave PTH-T and a nonapeptide. The nonapeptide was treated with trypsin and gave 2 peptides: (V-C-G-A) and (N-FF-W-K). Give the sequence of amino acid in the decapeptide.arrow_forwardSomatostatin is a tetradecapeptide of the hypothalamus that inhibits the release of pituitary growth hormone. Its amino acid sequence has been determined by a combination of Edman degradations and enzymic hydrolysis experiments. On the basis of the following data, deduce the primary structure of somatostatin: 1. Edman degradation gave PTH-Ala. 2. Selective hydrolysis gave peptides having the following indicated sequences: Phe-Trp Thr-Ser-Cys Lys-Thr-Phe Thr-Phe-Thr-Ser-Cys Asn-Phe-Phe-Trp-Lys Ala-Gly-Cys-Lys-Asn-Phe 3. Somatostatin has a disulfide bridge.arrow_forward
- Aspartame (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_forwardSerine esterase contains a catalytic triad at its active site. Which amino acid in serine esterase is responsible for mediating general acid catalysis for the breakdown of tetrahedral intermediate to the carboxyl product? Explain.arrow_forwardBrucine is a poisonous alkaloid obtained from Strychnos nux vomica, a tree that grows in India, Sri Lanka, and northern Australia. Write out a resolution scheme, which shows how a racemic mixture of phenylalanine can be resolved using brucine.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning