N-pentadecanoyl-L-Homoserine lactone Exclusive

Cayman Chemical Item Number 13094

C15-HSL (CAS 182359-66-6)

N-pentadecanoyl-L-Homoserine lactone (CAS 182359-66-6)

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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 C15-HSL is a product of Y. pseudituberculosis.5

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 Ortori, C.A., Atkinson, S., Chhabra, S.R., et al. Comprehensive profiling of N-acylhomoserine lactones produced by Yersinia pseudotuberculosis using liquid chromatography coupled to hybrid quadrupole-linear ion trap mass spectrometry. Anal Bioanal Chem 387 497-511 (2007).

Synonyms
  • C15-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​pentadecanamide
CAS Number 182359-66-6
Molecular Formula C19H35NO3
Formula Weight 325.5
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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CCCCCCCCCCCCCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C14H19NO2/c1-11(15-9-3-4-10-15)​14(16)​12-5-7-13(17-2)​8-6-12/h5-8,11H,3-4,9-10H2,1-2H3
InCHI Key
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QJWOQBGBEFNYKB-UHFFFAOYSA-N

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N-pentadecanoyl-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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Cart Total $0.00

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