177158-21-3

N-Nonanoyl-L-homoserine lactone Chemical Structure
177158-21-3

Chemical Structure

N-Nonanoyl-L-homoserine lactone

  • CAS No.: 177158-21-3
  • Formula:C13H23NO3
  • Molecular Weight:241.33

IUPAC Name: (S)-N-(2-oxotetrahydrofuran-3-yl)nonanamide

InChIKey: OMPXHNXRUVEQDO-NSHDSACASA-N

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

Biological Activity: Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial research for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in nutrient-rich Luria-Bertani broth (LB) medium.

Cat. No. Product Name Purity Description Pricing
HY-W127393
N-Nonanoyl-L-homoserine lactone Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial research for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in nutrient-rich Luria-Bertani broth (LB) medium.
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