N-tridecanoyl-L-Homoserine lactone Exclusive

Cayman Chemical Item Number 13093

C13-HSL (CAS 878627-21-5)

N-tridecanoyl-L-Homoserine lactone (CAS 878627-21-5)

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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 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.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
  • C13-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​tridecanamide
CAS Number 878627-21-5
Molecular Formula C17H31NO3
Formula Weight 297.4
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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CCCCCCCCCCCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C12H15NO3.ClH/c1-3-9(13-2)​12(14)​8-4-5-10-11(6-8)​16-7-15-10;/h4-6,9,13H,3,7H2,1-2H3;1H
InCHI Key
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KCJFEZQEDOBEOT-UHFFFAOYSA-N

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

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 2014-04-17. Prices are subject to change without notice.

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