| Identification | Back Directory | [Name]
C2-HSL, N-Acetyl-L-hoMoserine lactone | [CAS]
51524-71-1 | [Synonyms]
Acetyl-L-hoMoserine lactone
N-Acetyl-L-Homoserine Lactone
C2-HSL, N-Acetyl-L-hoMoserine lactone
(S)-N-(2-Oxotetrahydrofuran-3-yl)acetamide
Acetamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
(S)-N-(2-Oxotetrahydrofuran-3-yl)acetamide - [X92139]
2,2-dichloro-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide | [Molecular Formula]
C6H9NO3 | [MDL Number]
MFCD19160634 | [MOL File]
51524-71-1.mol | [Molecular Weight]
143.14 |
| Chemical Properties | Back Directory | [Melting point ]
82-84 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3)) | [Boiling point ]
441.3±34.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), DMF (Sparingly), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
14.78±0.20(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Description]
Acetyl-L-homoserine lactone belongs to the family of N-acylated homoserine lactones (HSLs) and has an acyl chain length of two carbons. HSLs perform a role in quorum sensing; however, unlike other HSLs, acetyl-L-homoserine lactone does not elicit a response in bacteria. In an assay of carbapenem antibiotic biosynthesis, acetyl-L-homoserine lactone does not induce a response in E. carotovora. In a fluorescence assay using E. coli containing a reporter plasmid of GFP expression in response to exogenous HSLs, acetyl-L-homoserine does not elicit GFP production. | [Uses]
Acetyl-L-homoserine lactone is the shortest alkyl homologue and most polar of a family of mediators of cel- t- cell interactions in bacterial biofilms. Acylhomoserine lactones have been detected in hundreds of bacterial species and, while the homologues vary between species and strains, the homoserine lactones are the major chemical modulators of within and between cell communication and regulation. Acetyl-L-homoserine lactone is not found in nature and can serve as a polar negative control for quorum sensing events. | [References]
[1] S R CHHABRA. Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone.[J]. Journal of Antibiotics, 1993, 46 3: 441-454. DOI: 10.7164/antibiotics.46.441
[2] MICHAIL SYRPAS. Haloperoxidase mediated quorum quenching by Nitzschia cf pellucida: study of the metabolization of N-acyl homoserine lactones by a benthic diatom.[J]. Marine Drugs, 2014, 12 1: 352-367. DOI: 10.3390/md12010352 |
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