Chapter 29: 23P (page 1177)
Devise a synthesis of each peptide from amino acid starting materials:
(a) Leu–Val; (b) Ala–Ile–Gly.
Chapter 29: 23P (page 1177)
Devise a synthesis of each peptide from amino acid starting materials:
(a) Leu–Val; (b) Ala–Ile–Gly.
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Get started for freeThe enolate derived from diethyl acetamidomalonate is treated with each of the following alkyl halides. After hydrolysis and decarboxylation, what amino acid is formed?
a. CH3I
b. (CH3)2CHCH2Cl
c. CH3CH2CH(CH3)Br
What aldehyde is needed to synthesize each amino acid by the Strecker synthesis?
(a) Valine;
(b) Leucine;
(c) Phenylalanine.
Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin,
appeared in Section 22.6B.)
Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:
a. What product is formed when glutathione reacts with an oxidizing agent?
b. What is unusual about the peptide bond between glutamic acid and cysteine?
Name each peptide using both the three-letter and one-letter abbreviations of the component amino acids.
a.
b.
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