216596-71-3

N-Undecanoyl-L-homoserine lactone Chemical Structure
216596-71-3

Chemical Structure

N-Undecanoyl-L-homoserine lactone

  • CAS No.: 216596-71-3
  • Formula:C15H27NO3
  • Molecular Weight:269.38

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

InChIKey: YAWJNUREPGJHSG-ZDUSSCGKSA-N

SMILES: CCCCCCCCCCC(N[C@H]1CCOC1=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. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.

Cat. No. Product Name Purity Description Pricing
HY-114773
N-Undecanoyl-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. C11-HSL has a rare odd-numbered acyl carbon chain and may be a minor quorum-sensing signaling molecule in Pseudomonas aeruginosa strains.
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This product is a controlled substance and not for sale in your territory.

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This compound is listed in the SVHC (Substances of Very High Concern) candidate list of ECHA (European Chemicals Agency).

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