N-butyryl-L-Homoserine lactone

Cayman Chemical Item Number 10007898

C4-HSL (CAS 67605-85-0)

N-butyryl-L-Homoserine lactone (CAS 67605-85-0)

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Description

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. 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-butyryl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing, controlling gene expression, and cellular metabolism.1 The diverse applications of this molecule include regulation of virulence in general, infection prevention, and formation of biofilms.2,3,4,5,6,7

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 Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

3 Diggle, S.P., Winzer, K., Lazdunski, A., et al. Advancing the quorum in pseudomonas aeruginosa: MvaT and the regulation of n-acylhomoserine lactone production and virulence gene expression. J Bacteriol 184(10) 2576-2586 (2002).

4 Pessi, G., Williams, F., Hindle, Z., et al. The global posttranscriptional regulator RsmA modulates production of virulence determinants and N-acylhomoserine lactones in pseudomonas aeruginosa. J Bacteriol 183(22) 6676-6683 (2001).

5 Hoang, T.T., and Schweizer, H.P. Characterization of pseudomonas aeruginosa enoyl-acyl carrier protein reductase (FabI): A target for the antimicrobial triclosan and its role in acylated homoserine lactone synthesis. J Bacteriol 181(17) 5489-5497 (1999).

6 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).

7 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).

Synonyms
  • C4-HSL
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​butanamide
CAS Number 67605-85-0
Molecular Formula C8H13NO3
Formula Weight 171.2
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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CCCC(=O)​N[C@H]​1CCOC1=O
InCHI Code
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​1S/C8H13NO3/c1-2-3-7(10)​9-6-4-5-12-8(6)​11/h6H,2-5H2,1H3,(H,9,10)​/t6-/m0/s1
InCHI Key
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VFFNZZXXTGXBOG-LURJTMIESA-N

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N-butyryl-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 2014-04-25. Prices are subject to change without notice.

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