Hydrazine cleaves amide bonds to form acylhydrazides according to the general mechanism of nucleophilic acyl substitution discussed in Chapter 20:
This reaction forms the basis of one method of terminal residue analysis. A peptide is treated with excess hydrazine in order to cleave all the peptide linkages. One of the terminal amino acids is cleaved as the free amino acid and identified; all the other amino acid residues are converted to acylhydrazides. Which amino acid is identified by hydrazinolysis, the N terminus or the C terminus?
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