Write what kind of reaction is each one of the four reactions depicted. (e.g. peptide bond formation, SN2 etc.) GLUCURONIC ACID SULPHATE CHCI, CHMO NO xox HO NO ON OSO, N 10, chloramphenicol: antibiotic prenalterol: B-blocker AMINO ACIDS MERCAPTURATES (Glutathione conjugates) CONHCH,COOH CH,CI OH ACNH COON OH ACNH ON ON YN COCK, CH.SCH,CHCOOK

Write what kind of reaction is each one of the four reactions depicted. (e.g. peptide bond formation, SN2 etc.) GLUCURONIC ACID SULPHATE CHCI, CHMO NO xox HO NO ON OSO, N 10, chloramphenicol: antibiotic prenalterol: B-blocker AMINO ACIDS MERCAPTURATES (Glutathione conjugates) CONHCH,COOH CH,CI OH ACNH COON OH ACNH ON ON YN COCK, CH.SCH,CHCOOK

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins

Section26.SE: Something Extra

Problem 49AP: Leuprolide is a synthetic nonapeptide used to treat both endometriosis in women and prostate cancer...

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When some sugars dissolve in water they spontaneously undergo changes in optical rotation called mutarrotation. The Mutarrotation of D-glucopyranose is catalyzed by acid and bases. 2-Hydroxypyridine is a more effective catalyst than phenol and pyridine for this reaction because: a.Both oxygen and N in 2-hydroxypyridine act as bases increasing the rapid interconversion of sugar b. The OH of 2-hydroxypyridine serves as the base while the current N as the acid. c. 2-hydroxypyridine acts both as a base to remove the proton from the hydroxyl group in the hemiacetal and as an acid to provide a proton to the oxygen in the hemiacetal. d.Phenol and pyridine are very expensive.
Bradykinin is a linear nonapeptide released by blood plasma globulin in response to a wasp sting. It is a very potent pain-causing agent. Its constituent amino acids are 2R, G, 2F, 3P, S. The sue of 2,4-dinitrofluorobenzene and carboxypeptidase shows that both terminal residues are arginine. Partial hydrolysis of bradykinin gives the following di- and tripeptides: FS + PGF +PP + SPF + FR + RP
Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.
Protein: SHAYNERSE Predict the products of the following reactions with the protein given, if there is none, write NO RXN. - Biuret reagent - KOH/Pb(CH2COO)2 - Glyoxilic Acid/Conc. H2SO - Hg/HNO3 - HNO3
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?
Predict the reactions ofcarbohydrates in acidic and basicsolutions, and with oxidizingand reducing agents
A nonapeptide released by globulins in the blood in response to a waspsting. Hydrolysis gives the following amino acids: 2 Arg, Gly, 2 Phe, 3 Pro, and Ser.Edman degradation gives phenylthiohydantoin of Arg. Cleavage with carboxypeptidase gives Arg. Partial hydrolysis gives the following di- and tripeptides: Phe-Ser, Pro-GlyPhe, Pro-Pro, Ser-Pro-Phe, Phe-Arg, and Arg-Pro. What is the amino acid sequence of this peptide?
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.
Another strategy used to resolve amino acids involves converting the carboxy group to an ester and then using a chiral carboxylic acid to carry out an acid–base reaction at the free amino group. Using a racemic mixture of alanine enantiomers and (R)-mandelic acid as resolving agent, write out the steps showing how a resolution process would occur.
Glutamic acid is a naturally occurring α-amino acid that contains acarboxy group in its R group side chain. (Glutamic acid isdrawn in its neutral form with no charged atoms, a form that does not actually exist at any pH.) a.) What form of glutamic acid exists at pH = 1?b.) If the pH is gradually increased, what form of glutamic acid exists afterone equivalent of base is added? After two equivalents? After threeequivalents?c.) Propose a structure of monosodium glutamate, the common flavorenhancer known as MSG.
consider a mixture of the following molecules glycine, 2-aminoethan-1-olate, ethanamine, ethanolate. which molecule will be in the orgnic layer after treatment with excess acid(e.g. HCl).
Is DL-Homocysteine soluble in ether?