Chapter 27: Problem 15
Why is Arg often referred to as a basic amino acid? Which other two amino acids are also basic amino acids?
Chapter 27: Problem 15
Why is Arg often referred to as a basic amino acid? Which other two amino acids are also basic amino acids?
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Get started for freeDinitrofluorobenzene, very often known as Sanger's reagent after the English chemist Frederick Sanger who popularized its use, reacts selectively with the \(N\)-terminal amino group of a polypeptide chain. Sanger was awarded the 1958 Nobel Prize in Chemistry for his work in determining the primary structure of bovine insulin. One of the few people to be awarded two Nobel Prizes, he also shared the 1980 award in chemistry with American chemists Paul Berg and Walter Gilbert for the development of chemical and biological analyses of DNA. Following reaction with 2,4 -dinitrofluorobenzene, all amide bonds of the polypeptide chain are hydrolyzed and the amino acid labeled with a 2,4-dinitrophenyl group is separated by either paper or column chromatography and identified. (a) 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. (b) When bovine insulin is treated with Sanger's reagent followed by hydrolysis of all peptide bonds, two labeled amino acids are detected: glycine and phenylalanine. What conclusions can be drawn from this information about the primary structure of bovine insulin? (c) Compare and contrast the structural information that can be obtained from use of Sanger's reagent with that from use of the Edman degradation.
A 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 \(\mathrm{H}_{2}\) 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.
What is the meaning of the alpha as it is used in \(\alpha\)-amino acid?
A decapeptide has the following amino acid composition. $$ \mathrm{Ala}_{2} \text {, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val } $$ Partial hydrolysis yields the following tripeptides. $$ \text { Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly } $$ One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.
Following is the primary structure of glucagon, a polypeptide hormone of 29 amino acids. Glucagon is produced in the \(\alpha\)-cells of the pancreas and helps maintain blood glucose levels in a normal concentration range. Which peptide bonds are hydrolyzed when this polypeptide is treated with each reagent? (a) Phenyl isothiocyanate (b) Chymotrypsin (c) Trypsin (d) \(\mathrm{BrCN}\)
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