Bergmann-Stern azlactone peptide synthesis

What is Bergmann-Stern azlactone peptide synthesis?

The Bergmann-Stern azlactone peptide synthesis, also known as Bergmann azlactone synthesis, is a process used to yield an acylated unsaturated dipeptide. This involves the conversion of an acetylated amino acid and an aldehyde into an azlactone with an alkylene side chain. Then, a second amino acid is added which undergoes ring opening, leading to the formation of the acylated unsaturated dipeptide. The dipeptide is subsequently catalytically hydrogenated and hydrolyzed to yield the final product.

Bergmann azlactone peptide synthesis
Bergmann-Stern azlactone peptide synthesis


Bergmann, M., Stern, F. and Witte, C. (1926), Über neue Verfahren der Synthese von Dipeptiden und Dipeptid-Anhydriden. [On new methods of synthesis of dipeptides and dipeptide anhydrides.] Justus Liebigs Ann. Chem., 449: 277-302.