N-(尾-ketocaproyl)-L-Homoserine lactone

货号： 10011207-10      产品名称： N-(尾-ketocaproyl)-L-Homoserine lactone   品牌： Cayman 规格： 10 mg 3周

N-(β-ketocaproyl)-L-Homoserine lactone
Cayman Chemical Item Number 10011207
Description Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1↗ This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.2↗ 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.3↗ 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.4↗ In one of the most-studied quorum-sensing systems in gram-negative bacteria, the LuxI AHL synthase catalyzes the production of N-(β-ketocaproyl)-L-homoserine lactone utilizing S-adenosylmethionine and hexanoyl-acyl carrier protein as reaction substrates in the marine bioluminescence bacterium V. fischeri.5↗ At increased populations of the bacteria, localized higher concentrations of 3-O-C6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence.1↗ Numerous other species of bacteria also employ N-(β-ketocaproyl)-L-homoserine lactone in cell-to-cell communication.6↗,7↗,8↗,9↗
Synonyms 3-O-C6-(L)-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​hexanamide
CAS Number 143537-62-6
Molecular Formula C10H15NO4
Formula Weight 213.2
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CCCC(=O)​CC(=O)​N[C@H]​1CCOC1=O 
InCHI Code ​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 

-20°C