Chapter 29: Q9. (page 1159)
Draw the products of each reaction.
(a)
(b)
(c)
(d)
Short Answer
(a)
(b)
(c)
(d)
Chapter 29: Q9. (page 1159)
Draw the products of each reaction.
(a)
(b)
(c)
(d)
(a)
(b)
(c)
(d)
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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 -nitrophenyl ester.
[2] Reaction of the -nitrophenyl ester with an amino acid ester
Draw the organic products formed in each reaction
What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson’s disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.
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?
What is the predominant form of each of the following amino acids at pH=11? What is the overall charge on the amino acid? (a)valine; (b)proline; (c)glutamic acid; (d)lysine?
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