O1764
N-(3-Oxooctanoyl)-L-homoserine lactone
≥97% (HPLC), white, powder
Synonym(s):
3-oxo-C8-HSL, 3OC8-HSL, N-(β-Ketooctanoyl)-L-homoserine
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About This Item
Empirical Formula (Hill Notation):
C12H19NO4
CAS Number:
Molecular Weight:
241.28
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32
MDL number:
SMILES string
CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChI key
FXCMGCFNLNFLSH-JTQLQIEISA-N
InChI
1S/C12H19NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h10H,2-8H2,1H3,(H,13,15)/t10-/m0/s1
assay
≥97% (HPLC)
form
powder
mol wt
241.28
technique(s)
protein expression: suitable
color
white
solubility
chloroform: 50 mg/mL, clear, colorless
shipped in
wet ice
storage temp.
−20°C
Quality Level
General description
N-(3-Oxooctanoyl)-L-homoserine lactone is a common quorum sensing (QS) signal.
It is a signaling molecule that is produced by Gram negative bacteria.
It is a signaling molecule that is produced by Gram negative bacteria.
Application
N-(3-Oxooctanoyl)-L-homoserine lactone has been used:
- to study the effects of pH, temperature, and salinity on extracellular polymeric substances (EPS) of Pseudomonas aeruginosa biofilm.
- as an AHL inducer to activate the quorum sensing pathways in Synechococcus elongatus.
Biochem/physiol Actions
N-(3-Oxooctanoyl)-L-homoserine lactone stimulates the tra gene expression. It is an autoinducer and potent antagonist.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Kayode K Ojo et al.
The Journal of antimicrobial chemotherapy, 57(6), 1065-1069 (2006-03-23)
To determine whether mef(A)-msr(D) and tet(M) genes are linked in representative Gram-negative isolates and/or transferred together during conjugation. To molecularly characterize the Acinetobacter junii element and compare the structure and sequence with the non-conjugative Streptococcus pneumoniae Tn2009 element. PCR assays
Z Q Luo et al.
Journal of bacteriology, 183(13), 3919-3930 (2001-06-08)
Conjugal transfer of Agrobacterium tumefaciens Ti plasmids is regulated by quorum sensing via TraR and its cognate autoinducer, N-(3-oxo-octanoyl)-L-homoserine lactone. We isolated four Tn5-induced mutants of A. tumefaciens C58 deficient in TraR-mediated activation of tra genes on pTiC58DeltaaccR. These mutations
Alessandro Vannini et al.
The EMBO journal, 21(17), 4393-4401 (2002-08-29)
The quorum sensing system allows bacteria to sense their cell density and initiate an altered pattern of gene expression after a sufficient quorum of cells has accumulated. In Agrobacterium tumefaciens, quorum sensing controls conjugal transfer of the tumour- inducing plasmid
Alessandro Vannini et al.
Acta crystallographica. Section D, Biological crystallography, 58(Pt 8), 1362-1364 (2002-07-24)
TraR is an Agrobacterium tumefaciens transcriptional regulator which binds the pheromone N-3-oxooctanoyl-L-homoserine lactone (AAI) in response to the bacterial population density. The TraR-AAI complex dimerizes and interacts with a specific 18-base-pair DNA sequence (TraBox), activating promoters containing this site. TraR
Effects of pH, Temperature and Salinity on Extracellular Polymeric
Substances of Pseudomonasaeruginosa Biofilm with
N-(3-Oxooxtanoyl)-L-Homoserine Lactone Addition
Substances of Pseudomonasaeruginosa Biofilm with
N-(3-Oxooxtanoyl)-L-Homoserine Lactone Addition
Lijie Zhou
J. Water Res. (2014)
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