N-(beta-ketocaproyl)-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 one of the most-studied quorum-sensing systems in gram-negative bacteria, the LuxI AHL synthase catalyzes the production of N-(beta-ketocaproyl)-L-homoserine lactone (N-(beta-ketocaproyl)-L-HSL) utilizing S-adenosylmethionine and hexanoyl-acyl carrier protein as reaction substrates in the marine bioluminescence bacterium V. fischeri. At increased populations of the bacteria, localized higher concentrations of N-(beta-ketocaproyl)-L-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence. Numerous other species of bacteria also employ N-(beta-ketocaproyl)-L-HSL in cell-to-cell communication.Formal Name: 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-hexanamide. CAS Number: 143537-62-6. Synonyms: 3-O-C6-(L)-HSL, N-(beta-ketocaproyl)-L-HSL. Molecular Formula: C10H15NO4. Formula Weight: 213.2. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, PBS (pH 7.2): 5 mg/ml. SMILES: CCCC(=O)CC(=O)N[C@H]1CCOC1=O. InChi Code: InChI=1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)/t8-/m0/s1. InChi Key: YRYOXRMDHALAFL-QMMMGPOBSA-N.