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
Elena V Piletska et al.
Biomacromolecules, 11(4), 975-980 (2010-03-17)
A first attempt to attenuate the quorum sensing (QS) of a marine heterotroph microorganism, Vibrio fischeri , using signal molecule-sequestering polymers (SSPs) is presented. A set of rationally designed polymers with affinity toward a signal molecule of V. fischeri
Yiling Cui et al.
Rapid communications in mass spectrometry : RCM, 23(8), 1212-1220 (2009-03-14)
A reversed-phase high-performance liquid chromatography/electrospray tandem mass spectrometry method was developed for the characterization of hydroxyl radical oxidation products of N-hexanoyl-homoserine lactone (C6-HSL), a member of the N-acylhomoserine lactone (AHL) class of microbial quorum-sensing signaling molecules identified in many Gram-negative
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