The 3-oxo-N-acyl-homoserine lactone (1  ) (3-oxo-AHL) is integral to the quorum sensing mechanism of pathogenic bacteria such as P.Aeruginosa. The reaction of hydrazine derivatives with the 3-oxo-AHL cleaves the substrate at the N-acyl bond to form the corresponding pyrazolone (2  ) in buffered conditions. The transformation is markedly enhanced through the use of an o-substituted aniline catalyst, supporting a mechanism of hydrazine condensation to the 3-oxo position followed by intramolecular nucleophilic attack. Conjugate addition of hydrazine to N-alkyl maleimides affords a series of particularly effective deacylating agents. This reactivity has inspired the derivitization of lysine residues and synthesis of short peptides capable of 3-oxo-AHL degradation. 

Deactivating the 3-oxo-<i>N</i>-acyl-homoserine lactone: Intramolecular amide cleavage through hydrazine condensation

246th National Meeting (2013)

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Deactivating the 3-oxo-N-acyl-homoserine lactone: Intramolecular amide cleavage through hydrazine condensation