Bergmann degradation

Overview
The Bergmann degradation is series of chemical reactions designed to remove a single amino acid from the carboxylic acid end of a peptide.



The acyl azide of a peptide (1) undergoes a Curtius rearrangement in the presence of benzyl alcohol (2) to give a benzyl carbamate (3). The Cbz group of intermediate 3 is removed by hydrogenolysis to give an unsubstituteda amide (4) and an aldehyde (5).