Organic Chemistry, 12e Study Guide/Student Solutions Manual
Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 24, Problem 15PP
Interpretation Introduction

Interpretation:

The explanation of structural features of a linker, which make it possible for the polypeptide to be detached from the Wang resin using trifluoroacetic acid, is to be given.

Concept introduction:

In solid-phase peptide synthesis (SPPS), peptides are prepared, residue by residue. The peptide is attached to polymer support at one end. The polymer support is insoluble; the by-products, excess reagents, and solvents are rinsed away in between each synthetic step and the polymer support remains intact.

The polypeptide is finally cleaved from the polymer support and is purified by HPLC (high-performance liquid chromatography). The Wang resin is used as polymer support for the batch synthesis of peptide acids following the Fmoc- or tert-Bu-protection. It is cleaved by TFA.

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Three peptides were obtained from a trypsin digestion of two different polypeptides. In each case, indicate the possible sequences from the given data and tell what further experiment should be carried out in order to determine the primary structure of the polypeptide. a. polypeptide I: 1. Val-Gly-Asp-Lys 2. Leu-Glu-Pro-Ala-Arg 3. Ala-Leu-Gly-Asp b. polypeptide II: 1. Val-Leu-Gly-Glu 2. Ala-Glu-Pro-Arg 3. Ala-Met-Gly-Lys
Deduce the sequence of a pentapeptide that contains the amino acids Ala, Glu, Gly, Ser, and Tyr, from the following experimental data. Edman degradation cleaves Gly from the pentapeptide, and carboxypeptidase forms Ala and a tetrapeptide. Treatment of the pentapeptide with chymotrypsin forms a dipeptide and a tripeptide. Partial hydrolysis forms Gly, Ser, and the tripeptide Tyr–Glu–Ala.
Three peptides were obtained from a trypsin digestion of two different polypeptides. indicate the possible sequences from the given data and tell what further experiment should be carried out in order to determine the primary structure of the polypeptide.  polypeptide I:         1. Val-Gly-Asp-Lys                     2. Leu-Glu-Pro-Ala-Arg 3. Ala-Leu-Gly-Asp
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