Organic Chemistry (Looseleaf) (Custom Package)
Organic Chemistry (Looseleaf) (Custom Package)
11th Edition
ISBN: 9781118757413
Author: Solomons
Publisher: WILEY
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Chapter 24, Problem 23P
Interpretation Introduction

Interpretation:

The heptapeptide sequence of amino acids, on the basis of the information provided, is to be deduced.

Concept introduction:

On treating a polypeptide with 2,4-dinitrofluorobenzene in basic solution, the free amino group of the N-terminal gives a nucleophilic aromatic substitution reaction, which, on hydrolysis, gives a mixture of amino acids in which the N-terminal amino acid is labeled with a 2,4-dinitrophenyl group. The C-terminal residues are identified through the carboxypeptidase enzymes. These enzymes catalyze the hydrolysis of the amide bond of the amino acid residue containing a free liberating carboxylic acid group.

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Determine the amino acid sequence of a polypeptide from the following data: Acid-catalyzed hydrolysis gives Ala, Arg, His, 2 Lys, Leu, 2 Met, Pro, 2 Ser, Thr, and Val. Carboxypeptidase A releases Val. Edman’s reagent releases PTH-Leu. Treatment with cyanogen bromide gives three peptides with the following amino acid compositions: 1. His, Lys, Met, Pro, Ser 2. Thr, Val 3. Ala, Arg, Leu, Lys, Met, Ser Trypsin-catalyzed hydrolysis gives three peptides and a single amino acid: 1. Arg, Leu, Ser 2. Met, Pro, Ser, Thr, Val 3. Lys 4. Ala, His, Lys, Met
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