R1 R, [1] [2] н OH Bọc-N н Bọc- OR' Bọc Н `NO, H2N, OR R2 p-nitrophenyl ester new amide bond in red -NO2 R1 Boc-N OCH3 p-methoxyphenyl ester

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins
Section26.4: Peptides And Proteins
Problem 9P: Draw the structure of M-P-V-G, and indicate its amide bonds.
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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.
a. Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation?
b. Would a p-methoxyphenyl ester perform the same function? Why or why not?

R1
R,
[1]
[2]
н
OH
Bọc-N
н
Bọc-
OR'
Bọc
Н
`NO, H2N,
OR
R2
p-nitrophenyl ester
new amide bond in red
-NO2
Transcribed Image Text:R1 R, [1] [2] н OH Bọc-N н Bọc- OR' Bọc Н `NO, H2N, OR R2 p-nitrophenyl ester new amide bond in red -NO2
R1
Boc-N
OCH3
p-methoxyphenyl ester
Transcribed Image Text:R1 Boc-N OCH3 p-methoxyphenyl ester
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