Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 24, Problem 13PP

Practice Problem 24.13

The synthesis of a polypeptide containing lysine requires the protection of both amino groups.

(a) Show how you might do this in a synthesis of the dipeptide KI using the ben-zyloxycarbonyl group as a protecting group.

(b) The benzyloxycarbonyl group can also be used to protect the guanidino group, N H | | N H C N H 2 , of arginine. Show a synthesis of the dipeptide RA.

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Consider the following peptide : Phe – Glu – Ser – Met and Val – Trp – Cys – Leu. Do these peptides have different net charges at (a) pH 1? (b) pH 7? Indicate the charges at both pH values
Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.
A tripeptide on hydrolysis produced glycine, alanine and leucine.  The structures of these amino acids are shown below.  On reaction with Edman’s reagent, leucine was released as the phenylhydantoin. Treatment of the tripeptide with carboxypeptidase gave glycine. Draw the structure of the tripeptide.
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