Chapter 29: Q14. (page 1166)
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.
a. Val–Glu
b. Gly–His–Leu
c. M–A–T–T
Short Answer
a.
b.
c.
Chapter 29: Q14. (page 1166)
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide bonds.
a. Val–Glu
b. Gly–His–Leu
c. M–A–T–T
a.
b.
c.
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Get started for freeAnother method to form a peptide bond involves a two-step process:
[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.
[2] Reaction of the p-nitrophenyl ester with an amino acid ester.
Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation?
Would a p-methoxyphenyl ester perform the same function? Why or why not?
Outline the steps needed to synthesize the tetrapeptideAla–Leu–Ile–Gly using the Merrifield technique.
L-thyroxine, a thyroid hormone and oral medication used to treat thyroid hormone deficiency, is an amino acid that does not exist in proteins. Draw the zwitterionic form of L-thyroxine.
Deduce the sequence of a heptapeptide that contains the amino acids Ala, Arg, Glu, Gly, Leu, Phe, and Ser, from the following experimental data. Edman degradation cleaves Leu from the heptapeptide, and carboxypeptidase forms Glu and a hexapeptide. Treatment of the heptapeptide with chymotrypsin forms a hexapeptide and a single amino acid. Treatment of the heptapeptide with trypsin forms a pentapeptide and a dipeptide. Partial hydrolysis forms Glu, Leu, Phe, and the tripeptidesGly–Ala–Ser and Ala–Ser–Arg
Draw the organic products formed in each reaction
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