Chapter 29: 61P (page 1196)
Draw all the steps in the synthesis of each peptide from individual amino acids:
Gly-Ala;
- Ile-Ala-Phe
Chapter 29: 61P (page 1196)
Draw all the steps in the synthesis of each peptide from individual amino acids:
Gly-Ala;
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Get started for freeQuestion: Identify A and B, isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{4}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\), from the given \({}^{\bf{1}}{\bf{H}}\)NMR data: Compound A exhibits signals at 1.75 (doublet, 3H,\({\bf{J = 6}}{\bf{.9 Hz}}\)) and 5.89 (quartet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 6}}{\bf{.9 Hz}}\)) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, \({}^{\bf{1}}{\bf{H}}\),\({\bf{J = 1}}{\bf{.9 Hz}}\)), and 5.59 (doublet, \({}^{\bf{1}}{\bf{H}}\), \({\bf{J = 1}}{\bf{.9 Hz}}\)) ppm.
An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glue (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile-Leu in addition to other products. Deduce the structure of the octapeptide and fragments A-D.
Glutathione, a powerful antioxidant that destroys harmful oxidizing agents in cells, is composed of glutamic acid, cysteine, and glycine, and has the following structure:
Glutathione
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?
Devise a synthesis of the following dipeptide from amino acid starting materials.
Outline the steps needed to synthesize the tetrapeptideAla–Leu–Ile–Gly using the Merrifield technique.
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