N-nonanoyl-L-Homoserine lactone

Cayman Chemical Item Number 16868

C9-HSL (CAS 177158-21-3)

N-nonanoyl-L-Homoserine lactone (CAS 177158-21-3)

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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 C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in the nutrient-rich Luria-Bertani Broth (LB) medium.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 Brader, G., Sjöblom, S., Hyytiäinen, H., et al. Altering substrate chain length specificity of an acylhomoserine lactone synthase in bacterial communication. J Biol Chem 280(11) 10403-10409 (2005).

Synonyms
  • C9-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​nonanamide
CAS Number 177158-21-3
Molecular Formula C13H23NO3
Formula Weight 241.3
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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CCCCCCCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C13H23NO3/c1-2-3-4-5-6-7-8-12(15)​14-11-9-10-17-13(11)​16/h11H,2-10H2,1H3,(H,14,15)​/t11-/m0/s1
InCHI Key
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OMPXHNXRUVEQDO-NSHDSACASA-N

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Size Price Quantity Subtotal
5 mg $26.00 $0.00
10 mg $49.00 $0.00
25 mg $117.00 $0.00
50 mg $208.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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