N-octadecanoyl-L-Homoserine lactone Exclusive

Cayman Chemical Item Number 13209

C18-HSL (CAS 479050-96-9)

N-octadecanoyl-L-Homoserine lactone (CAS 479050-96-9)

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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 C18-HSL is one of four lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum sensing signaling in strains of S. meliloti, a nitrogen-fixing bacterial symbiont of the legume M. sativa.5 C18-HSL and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.6,7

1 González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70(4) 859-875 (2006).

2 Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J Bacteriol 188(2) 773-783 (2006).

3 Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nat Rev Microbiol 6(1) 17-27 (2008).

4 Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions. FEBS Lett 580 561-567 (2006).

5 Marketon, M., Gronquist, M.R., Eberhard, A., et al. Characterization of the Sinorhizobium meliloti sinR/sinI locus and the production of novel N-Acyl homoserine lactones. J Bacteriol 184(20) 5686-5695 (2002).

6 Pearson, J.P., Van Delden, C., and Iglewski, B.H. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals. J Bacteriol 181(4) 1203-1210 (1999).

7 Mashburn-Warren, L., and Whiteley, M. Special delivery: Vesicle trafficking in prokaryotes. Mol Microbiol 61(4) 839-846 (2006).

Synonyms
  • C18-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​octadecanamide
CAS Number 479050-96-9
Molecular Formula C22H41NO3
Formula Weight 367.6
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1[C@@H]​(NC(CCCCCCCCCCCCCCCCC)​=O)​CCO1
InCHI Code
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​1S/C22H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)​23-20-18-19-26-22(20)​25/h20H,2-19H2,1H3,(H,23,24)​/t20-/m0/s1
InCHI Key
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HGMDJDYXARRSKB-FQEVSTJZSA-N

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N-octadecanoyl-L-Homoserine lactone is available in the following screening library:

Size Price Quantity Subtotal
5 mg $30.00 $0.00
10 mg $57.00 $0.00
25 mg $135.00 $0.00
50 mg $240.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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