N-hexanoyl-L-Homoserine lactone

Cayman Chemical Item Number 10007896

C6-HSL (CAS 147852-83-3)

N-hexanoyl-L-Homoserine lactone (CAS 147852-83-3)

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Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-hexanoyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and affecting cellular metabolism.1 The diverse applications of this molecule include regulation of virulence in general and in cystic fibrosis, infection prevention, slime and biofilm reduction in commercial agriculture and aquaculture industries, food spoilage prevention, and septicemia in fish.2,3,4,5,6,7,8

1 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).

2 Morohoshi, T., Inaba, T., Kato, N., et al. Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen edwardsiella tarda. J Biosci Bioeng 98(4) 274-281 (2004).

3 Ulrich, R.L., Hines, H.B., Parthasarathy, N., et al. Mutational analysis and biochemical characterization of the bukholderia thailandensis DW503 quorum-sensing network. J Bacteriol 186(13) 4350-4360 (2004).

4 Wang, L., Weng, L., Dong, Y., et al. Specificity and enzyme kinetics of the quorum-quenching N-acyl homoserine lactone lactonase (AHL-lactonase). J Biol Chem 279(14) 13645-13651 (2004).

5 Yates, E.A., Philipp, B., Buckley, C., et al. N-acylhomoserine lactones undergo lactonolysis in a pH-temperature-, and acyl chain length-dependent manner during growth of yersinia pseudotuberculosis and pseudomonas aeruginosa. Infect Immun 70(10) 5635-5646 (2002).

6 Luo, Z., Su, S., and Farrand, S.K. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: Kinetics and consequences. J Bacteriol 186(19) 5665-5672 (2003).

7 Christensen, A.B., Riedel, K., Eberl, L., et al. Quorum-sensing-directed protein expression in serratia proteamaculans B5a. Microbiology 149 471-483 (2003).

8 Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett 244 297-304 (2005).

Synonyms
  • C6-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​hexanamide
CAS Number 147852-83-3
Molecular Formula C10H17NO3
Formula Weight 199.2
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C10H17NO3/c1-2-3-4-5-9(12)​11-8-6-7-14-10(8)​13/h8H,2-7H2,1H3,(H,11,12)​/t8-/m0/s1
InCHI Key
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ZJFKKPDLNLCPNP-QMMMGPOBSA-N

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

Size Price Quantity Subtotal
5 mg $14.00 $0.00
10 mg $27.00 $0.00
25 mg $63.00 $0.00
50 mg $112.00 $0.00
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Pricing updated 2014-04-18. Prices are subject to change without notice.

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