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- Show how the following amino acids might be formed in the laboratory by reductiveamination of the appropriate a@ketoacid. serineBrucine 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.Although tryptophan contains a heterocyclic amine, it is considered a neutral aminoacid. Explain why the indole nitrogen of tryptophan is more weakly basic than one ofthe imidazole nitrogens of histidine.
- Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteineresidues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione givesGly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released.Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1246), followed bycomplete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenylisothiocyanate does not give a recognizable phenylthiohydantoin, however.(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normalproduct from Edman degradation, even though it gives a normal product from the Sanger reagent followed byhydrolysis?(b) Oxidation of glutathione forms glutathione disulfide (GSSG). Propose a structure for glutathione disulfide, and…(a) Isoleucine has been prepared by the following sequence of reactions. Give the structure of compounds A through D isolated as intermediates in this synthesis.(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide would you choose as the starting material for this synthesis?Write a structural formula for the product formed by treatment of the N-terminal amino group with Sanger’s reagent and propose a mechanism for its formation.
- Show how phenylalanine can be prepared by reductive amination of an α-ketocarboxylic acid.4b) Canavanine is closely related to arginine, and like arginine its side group has a +1 charge when protonated. If you dissolved canavanine in an aqueous solution at pH 10, what would the net charge on a molecule of canavanine be? Please show your work or make it clear how you determined the charge contribution from each ionizable group.Esterase 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?
- -Amino acids can be prepared by the Strecker synthesis, a two-step process in which an aldehyde is treated with ammonium cyanide followed by hydrolysis of the amino nitrile intermediate with aqueous acid. Propose a mechanism for the reaction.Leuprolide 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?Which of the following substituent is a meta-directing deactivator? a amino group b halogenation group c phenyl group d carboxyl group