We saw in Section 25.6 that DCC can be used to form a pe
Question and Solution
We saw in Section 25.6 that DCC can be used to form a peptide bond. We explored the mechanism, and we saw that DCC activ
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We saw in Section 25.6 that DCC can be used to form a peptide bond. We explored the mechanism, and we saw that DCC activates the COOH moiety so that it readily undergoes nucleophilic acyl substitution. An alternative method for activating a COOH group involves converting it into an activated ester, such as a para-nitrophenyl ester: The activated ester is readily attacked by a suitably protected amino acid to form a peptide bond: (a) Explain how the p-nitrophenyl ester activates the carbonyl group toward nucleophilic acyl substitution. (b) What is the function of the nitro group? (c) A meta-nitrophenyl ester is less activating than a paranitrophenyl ester. Explain.
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