N-3-oxo-hexadec-11(Z)-enoyl-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. An unspecified positional and geometric isomer of 3-oxo-C16:1-(L)-HSL is produced by the F2/5 strain of A. vitis, the bacterium responsible for grape crown gall and its resulting loss of agricultural productivity.Formal Name: 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-(11Z)-hexadecenamide. CAS Number: 1269663-80-0. Synonyms: 3-oxo-C16:1-Delta11cis-(L)-HSL. Molecular Formula: C20H33NO4. Formula Weight: 351.5. Purity: >98%. Formulation: (Request formulation change), A solution in acetonitrile. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml. lambdamax: 246 nm. SMILES: O=C1[C@@H](NC(CC(CCCCCCC/C=C\CCCC)=O)=O)CCO1. InChi Code: InChI=1S/C20H33NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-19(23)21-18-14-15-25-20(18)24/h5-6,18H,2-4,7-16H2,1H3,(H,21,23)/b6-5-/t18-/m0/s1. InChi Key: UKVJHGAETBFGBY-XFHJGTJQSA-N.