Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.9C, Problem 24.21P

(a)

Interpretation Introduction

To determine: The mechanism for the reaction of the N terminus of the peptide with 2,4-dinitrofluorobenzene.

Interpretation: The mechanism for the reaction of the N terminus of the peptide with 2,4-dinitrofluorobenzene is to be determined.

Concept introduction: The process in which a proper series of amino acids is maintained in the  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)

Interpretation Introduction

To determine: The reason that the Edman degradation is usually preferred over the Sanger method.

Interpretation: The reason that the Edman degradation is usually preferred over the Sanger method is to be determined.

Concept introduction: The process in which a proper series of amino acids is maintained in the  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.

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An 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.
A peptide has the following amino acid composition: 2 Met, 2 Phe, 2 Glu, 1 Arg, 1 Lys, 1 Val, 1 Leu, 1 Gly, 1 Ser Reaction of the intact peptide with dansyl chloride followed by acid hydrolysis creates a derivative of Met. A specific cleavage of the intact peptide produces fragments with the following sequences: Fragment A: Glu-Gly-Lys-Phe Fragment B: Met-Ser-Leu-Arg Fragment C: Met-Val-Glu-Phe   What information do this result give about the sequence of the peptide? Explain how you arrived on your answer. a) The sequence is: Met-Val-Glu-Phe-Glu-Gly-Lys-Phe-Met-Ser-Leu-Arg b) The sequence is: Met-Ser-Leu-Arg-Met-Val-Glu-Phe-Glu-Gly-Lys-Phe c) The sequence is: Met-Val-Glu-Phe-Met-Ser-Leu-Arg-Glu-Gly-Lys-Phe d) The sequence is: Met-Ser-Leu-Arg-Glu-Gly-Lys-Phe-Met Val-Glu-Phe
Show the peptides that would result from cleavage by the indicated reagent: Val-Arg-Gly-Met-Arg-Ala-Ser by carboxypeptidase A

Chapter 24 Solutions

Organic Chemistry (9th Edition)

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