N-tridecanoyl-L-Homoserine lactone [878627-21-5]

TargetMol Chemicals

N-tridecanoyl-L-Homoserine lactone [878627-21-5]

16

878627-21-5

Chemical

Research Use Only

N-tridecanoyl-L-Homoserine lactone

C17H31NO3

297.43

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. N-tridecanoyl-L-Homoserine lactone (C13-HSL) possesses a rare odd-numbered acyl carbon chain and is produced by wild-type and mutant strains of Y. pseudotuberculosis in trace amounts.

3 years

N(C(CCCCCCCCCCCC)=O)[C@@H]1C(=O)OCC1

-20°C

12352209