N-3-oxo-octanoyl-L-Homoserine lactone

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases. AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. In the gram-negative bacterium A. tumefaciens, N-3-oxo-octanoyl-L-homoserine lactone promotes the expression of the transcriptional activator (and LuxR homolog) TraR.Formal Name: 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide. CAS Number: 147795-39-9. Synonyms: 3-oxo-C8-HSL, N-beta-oxo-octanoyl-L-Homoserine lactone. Molecular Formula: C12H19NO4. Formula Weight: 241.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml. SMILES: O=C1[C@@H](NC(CC(CCCCC)=O)=O)CCO1. InChi Code: InChI=1S/C12H19NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h10H,2-8H2,1H3,(H,13,15)/t10-/m0/s1. InChi Key: FXCMGCFNLNFLSH-JTQLQIEISA-N.