| Identification | Back Directory | [Name]
N-phenylacetyl-L-Homoserine lactone | [CAS]
55154-48-8 | [Synonyms]
N-phenylacetyl-L-Homoserine lactone
N-[(3S)-2-oxooxolan-3-yl]-2-phenylacetamide
NphenylacetylLHomoserine lactone,N phenylacetyl L Homoserine lactone | [Molecular Formula]
C12H13NO3 | [MOL File]
55154-48-8.mol | [Molecular Weight]
219.24 |
| Chemical Properties | Back Directory | [Melting point ]
130.7-132.0 °C | [Boiling point ]
518.8±49.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; PBS (pH 7.2): 0.1 mg/ml | [form ]
A crystalline solid | [pka]
14.66±0.20(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [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. Autoinducers containing a phenylacetanoyl group in the acyl chain display a wide range of inhibitory and activating effects on various R protein transcriptional regulators.3,4,5 N-phenylacetyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing in the model symbiont V. fischeri and the pathogens A. tumefaciens and P. aeruginosa.5,6 It has been reported to antagonize TraR signaling in A. tumefaciens, LasR signaling in E. coli, and LuxR signaling in V. fischeri.4 | [storage]
Store at -20°C | [References]
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. Geske, G.D., O'Neill, J.C., and Blackwell, H.E. N-phenylacetanoyl-L-homoserine lactones can strongly antagonize or superagonize quorum sensing in Vibrio fischeri ACS Chem. Biol. 2(5),315-319(2007).
4. Geske, G.D., O'Neill, J.C., Miller, D.M., et al. Comparative analyses of N-acylated homoserine lactones reveal unique structural features that dictate their ability to activate or inhibit quorum sensing Chembiochem 9(3),389-400(2008).
5. Geske, G.D., O'Neill, J.C., Miller, D.M., et al. Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N-acylated homoserine lactones in multiple species and new insights into their mechanisms of action J. Am. Chem. Soc. 129,13613-13625(2007).
6. Geske, G.D., Wezeman, R.J., Siegel, A.P., et al. Small molecule inhibitors of bacterial quorum sensing and biofilm formation J. Am. Chem. Soc. 127(37),12762-12763(2005). |
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