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

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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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