Bergmann degradation

The Bergmann degradation is series of chemical reactions designed to remove a single amino acid from the carboxylic acid end of a peptide.^[1][2]

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).

• Curtius rearrangement
• Edman degradation

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