N-Nonanoyl-L-homoserine lactone

N-Acyl homoserine lactones (AHLs) are a class of autoinducers used by bacteria in quorum sensing, a regulatory system controlling gene expression in response to increased cell density. This regulation leads to diverse phenotypes, such as biofilm formation and production of virulence factors. Coordinated gene expression is achieved through the generation, release, and detection of small diffusible signal molecules called autoinducers. AHLs typically consist of fatty acids linked to homoserine lactone (HSL). Modulating bacterial quorum sensing signal systems to suppress pathogenesis offers a novel antimicrobial approach in studying infectious diseases. AHLs vary in acyl chain length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo groups), and the presence or absence of carbon-carbon double bonds, providing signal specificity via LuxR family transcription factors. C9-HSL, characterized by an unusual odd-numbered acyl carbon chain, is produced by the wild-type Erwinia carotovora subsp. carotovora strain SCC 3193 grown in nutrient-rich Luria-Bertani broth (LB).

177158-21-3

C13H23NO3

241.33

CCCCCCCCC(N[C@@H]1C(OCC1)=O)=O