| Identification | Back Directory | [Name]
N-hexanoyl-L-homoserine lactone | [CAS]
147852-83-3 | [Synonyms]
C6-HSL
C6HSL,HHL
Hexanoyl-L-hoMoserine lactone
N-hexanoyl-L-homoserine lactone
N-[(3S)-2-oxooxolan-3-yl]hexanamide
C6-HSL, N-Hexanoyl-L-hoMoserine lactone
N-[(3S)-Tetrahydro-2-oxo-3-furanyl]hexanamide
Hexanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]- | [Molecular Formula]
C10H17NO3 | [MDL Number]
MFCD12912260 | [MOL File]
147852-83-3.mol | [Molecular Weight]
199.25 |
| Chemical Properties | Back Directory | [Melting point ]
132-134 °C(Solv: dichloromethane (75-09-2)) | [Boiling point ]
434.0±34.0 °C(Predicted) | [density ]
1.08±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml | [form ]
A crystalline solid | [pka]
15.03±0.20(Predicted) | [color ]
White to light yellow | [Optical Rotation]
[α]/D -32±3°, c = 0.2 in methanol | [BRN ]
8143287 |
| Hazard Information | Back Directory | [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. 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. | [Uses]
Hexanoyl-L-homoserine lactone is an active quorum sensing modulator first recognised in Rhizobium leguminosarum. Hexanoyl-L-homoserine lactone and other 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. The most significant variable defining the function of the homoserine lactone is the length of the acyl chain, with shorter chains displaying opposing actions to the longer chains. | [Definition]
ChEBI: N-[(3s)-2-Oxotetrahydrofuran-3-Yl]hexanamide is a N-acyl-amino acid. | [General Description]
N-Hexanoyl-L-homoserine lactone is produced and utilized by various Gram-negative bacteria as a quorum sensing (QS) signal molecule. | [Biochem/physiol Actions]
N-Hexanoyl-L-homoserine lactone is a member of N-acyl-homoserine lactone family. N-Acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella, and are involved in quorum sensing, cell to cell communication among bacteria; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation. | [References]
[1] TOMOHIRO MOROHOSHI . Identification of quorum-sensing signal molecules and the LuxRI homologs in fish pathogen Edwardsiella tarda[J]. Journal of bioscience and bioengineering, 2004, 98 4: Pages 274-281. DOI: 10.1016/s1389-1723(04)00281-6
[2] RICKY L ULRICH. Mutational analysis and biochemical characterization of the Burkholderia thailandensis DW503 quorum-sensing network.[J]. Journal of Bacteriology, 2004, 186 13: 4350-4360. DOI: 10.1128/jb.186.13.4350-4360.2004
[3] LIAN-HUI WANG. Specificity and enzyme kinetics of the quorum-quenching N-Acyl homoserine lactone lactonase (AHL-lactonase).[J]. The Journal of Biological Chemistry, 2004, 279 14: 13645-13651. DOI: 10.1074/jbc.m311194200
[4] EDWIN A YATES. N-acylhomoserine lactones undergo lactonolysis in a pH-, temperature-, and acyl chain length-dependent manner during growth of Yersinia pseudotuberculosis and Pseudomonas aeruginosa.[J]. Infection and Immunity, 2002, 70 10: 5635-5646. DOI: 10.1128/iai.70.10.5635-5646.2002
[5] ZHAO-QING LUO S K F Shengchang Su. In situ activation of the quorum-sensing transcription factor TraR by cognate and noncognate acyl-homoserine lactone ligands: kinetics and consequences.[J]. Journal of Bacteriology, 2003, 185 19: 5665-5672. DOI: 10.1128/jb.185.19.5665-5672.2003
[6] ALLAN B CHRISTENSEN. Quorum-sensing-directed protein expression in Serratia proteamaculans B5a.[J]. Microbiology-Sgm, 2003, 149 Pt 2: 471-483. DOI: 10.1099/mic.0.25575-0
[7] CATHERINE E. CHAMBERS. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients[J]. Fems Microbiology Letters, 2006, 244 2: 297-304. DOI: 10.1016/j.femsle.2005.01.055 |
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