Chapter 29: Question 29.68 (page 1197)
Devise a stepwise synthesis of the tripeptide Val-leu-Val from 3-methylbutanal as the only organic starting material. You may also use any required inorganic or organic reagents.
Short Answer
Answer


Chapter 29: Question 29.68 (page 1197)
Devise a stepwise synthesis of the tripeptide Val-leu-Val from 3-methylbutanal as the only organic starting material. You may also use any required inorganic or organic reagents.
Answer


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What types of stabilizing interactions exist between each of the following pairs of amino acids?
a. Ser and Tyr
b. Val and Leu
c. two Phe residues
Another 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?

Identify the lettered intermediates in the following reaction scheme. This is an alternative method to synthesize amino acids, based on the Gabriel synthesis of 1° amines (Section 25.7A).

Question: Identify the functional groups in each molecule. Classify each alcohol, alkyl halide, amide, and amine as 1°, 2°, or 3°
a.
b.
c. 
d. 
e. 
f. 
What form exists at the isoelectric point of each of the following amino acids: (a) valine; (b)leucine; (c)proline; (d) glutamic acid.
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