K3255
N-(β-Ketocaproyl)-DL-homoserine lactone
analytical standard
Synonym(s):
N-(3-Oxohexanoyl)-DL-homoserine lactone
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About This Item
Empirical Formula (Hill Notation):
C10H15NO4
CAS Number:
Molecular Weight:
213.23
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
InChI
1S/C10H15NO4/c1-2-3-7(12)6-9(13)11-8-4-5-15-10(8)14/h8H,2-6H2,1H3,(H,11,13)
SMILES string
CCCC(=O)CC(=O)NC1CCOC1=O
InChI key
YRYOXRMDHALAFL-UHFFFAOYSA-N
grade
analytical standard
technique(s)
HPLC: suitable, gas chromatography (GC): suitable
suitability
suitable for manufacturing use
application(s)
forensics and toxicology
pharmaceutical (small molecule)
veterinary
format
neat
storage temp.
−20°C
Quality Level
Application
N-(β-Ketocaproyl)-DL-homoserine lactone has been used as a reference standard in identifying the quorum sensing signal molecules released by the in wood samples affected by Brenneria salicis bacteria bacteria, using ultra-high performance liquid chromatography coupled with an ion-trap mass spectrometer.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
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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Zamia Diaz et al.
PloS one, 4(8), e6820-e6820 (2009-08-29)
Many bacteria produce and respond to the quorum sensing signal autoinducer-2 (AI-2). Escherichia coli and Salmonella typhimurium are among the species with the lsr operon, an operon containing AI-2 transport and processing genes that are up regulated in response to
Yunrong Chai et al.
Journal of bacteriology, 191(11), 3706-3711 (2009-03-31)
TraR of Agrobacterium tumefaciens is a LuxR-type quorum-sensing transcription factor that regulates genes required for replication and conjugation of the tumor-inducing (Ti) plasmid. TraR requires its cognate autoinducer N-3-oxooctanoyl-homoserine lactone (OOHL) for resistance of proteolysis in wild-type bacteria and for
D Krysciak et al.
Applied and environmental microbiology, 77(15), 5089-5099 (2011-06-07)
Rhizobium sp. strain NGR234 is a unique alphaproteobacterium (order Rhizobiales) that forms nitrogen-fixing nodules with more legumes than any other microsymbiont. Since we have previously described the complete genome sequence of NGR234, we now report on a genome-wide functional analysis
Tao Long et al.
PLoS biology, 7(3), e68-e68 (2009-03-27)
Cell-to-cell communication in bacteria is a process known as quorum sensing that relies on the production, detection, and response to the extracellular accumulation of signaling molecules called autoinducers. Often, bacteria use multiple autoinducers to obtain information about the vicinal cell
Guoping Jin et al.
Biochemical and biophysical research communications, 417(3), 991-995 (2011-12-31)
Many Gram-negative bacteria use N-acyl-homoserine lactones (AHLs) as quorum sensing (QS) signaling molecules to coordinate their group behavior. Recently, it was shown that plants can perceive and respond to these bacterial AHLs. However, little is known about the molecular mechanism
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