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N-(β-ketocaproyl)-L-Homoserine lactone

Cayman Chemical Item Number 10011207

3-O-C6-(L)-HSL (CAS 143537-62-6)

N-(β-ketocaproyl)-L-Homoserine lactone (CAS 143537-62-6)

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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 In one of the most-studied quorum-sensing systems in gram-negative bacteria, the LuxI AHL synthase catalyzes the production of N-(β-ketocaproyl)-L-homoserine lactone utilizing S-adenosylmethionine and hexanoyl-acyl carrier protein as reaction substrates in the marine bioluminescence bacterium V. fischeri.5 At increased populations of the bacteria, localized higher concentrations of 3-O-C6-HSL, an endogenous ligand to transcriptional factor LuxR, leads to increased production of both the AHL synthase and proteins responsible for bioluminescence.1 Numerous other species of bacteria also employ N-(β-ketocaproyl)-L-homoserine lactone in cell-to-cell communication.6,7,8,9

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 Schaefer, A.L., Val, D.L., Hanzelka, B.L., et al. Generation of cell-to-cell signals in quorum sensing: Acyl homoserine lactone synthase activity of a purified Vibrio fischeri LuxI protien. Proc Natl Acad Sci USA 93 9505-9509 (1996 Sep).

6 Welch, M., Todd, D.E., Whitehead, N.A., et al. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J 19(4) 631-641 (2000).

7 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).

8 Toth, I.K., Newton, J.A., Hyman, L.J., et al. Potato plants genetically modified to produce N-acylhomoserine lactones increase susceptibility to soft rot erwiniae. Mol Plant Microbe Interact 17(8) 880-887 (2004).

9 Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 153 3923-3938 (2007).

Synonyms
  • 3-O-C6-(L)-HSL
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​hexanamide
CAS Number 143537-62-6
Molecular Formula C10H15NO4
Formula Weight 213.2
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCC(=O)​CC(=O)​N[C@H]​1CCOC1=O

Background Reading

González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70(4) 859-875 (2006).

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).

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).

Schaefer, A.L., Val, D.L., Hanzelka, B.L., et al. Generation of cell-to-cell signals in quorum sensing: Acyl homoserine lactone synthase activity of a purified Vibrio fischeri LuxI protien. Proc Natl Acad Sci USA 93 9505-9509 (1996 Sep).

Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 153 3923-3938 (2007).

Welch, M., Todd, D.E., Whitehead, N.A., et al. N-acyl homoserine lactone binding to the CarR receptor determines quorum-sensing specificity in Erwinia. EMBO J 19(4) 631-641 (2000).

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).

Toth, I.K., Newton, J.A., Hyman, L.J., et al. Potato plants genetically modified to produce N-acylhomoserine lactones increase susceptibility to soft rot erwiniae. Mol Plant Microbe Interact 17(8) 880-887 (2004).

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).

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Size Price Quantity Subtotal
5 mg $23.00 $0.00
10 mg $44.00 $0.00
25 mg $104.00 $0.00
50 mg $184.00 $0.00
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Pricing updated 2012-05-25. Prices are subject to change without notice.

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