Chapter 27: Problem 12
Define the term zwitterion.
Short Answer
Step by step solution
Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chapter 27: Problem 12
Define the term zwitterion.
These are the key concepts you need to understand to accurately answer the question.
All the tools & learning materials you need for study success - in one app.
Get started for free2,4-Dinitrofluorobenzene, 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 for chemistry for his work in determining the primary structure of bovine insulin. One of the few persons 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.
How many different tetrapeptides can be made under the following conditions? (a) The tetrapeptide contains one unit each of Asp, Glu, Pro, and Phe. (b) All 20 amino acids can be used, but each only once.
From which amino acid are serotonin and melatonin synthesized, and what types of reactions are involved in their biosynthesis? a. b.
At pH 7.4, with what amino acid side chains can the side chain of lysine form salt linkages?
A tetradecapeptide (14 amino acid residues) gives the following peptide fragments on partial hydrolysis. From this information, deduce the primary structure of this polypeptide. Fragments are grouped according to size. $$ \begin{array}{ll} \hline \text { Pentapeptide Fragments } & \text { Tetrapeptide Fragments } \\ \hline \text { Phe-Val-Asn-Gln-His } & \text { Gln-His-Leu-Gys } \\ \text { His-Leu-Cys-Gly-Ser } & \text { His-Leu-Val-Glu } \\ \text { Gly-Ser-His-Leu-Val } & \text { Leu-Val-Glu-Ala } \\ \hline \end{array} $$
What do you think about this solution?
We value your feedback to improve our textbook solutions.