N-(Ketocaproyl)-D,L-homoserine lactone

Names

[ Name ]:
N-(Ketocaproyl)-D,L-homoserine lactone

[Synonym ]:
n-(ketocaproyl)-d,l-homoserine lactone
N-(3-oxohexanoyl)-L-homoserine lactone
Hexanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]hexanamide

Biological Activity

[Description]:

N-(Ketocaproyl)-D,L-homoserine lactone is a natural, very active ligand of LuxR. N-(Ketocaproyl)-D,L-homoserine lactone is a quorum sensing (QS) autoinducer[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

N-(Ketocaproyl)-D,L-homoserine lactone is a natural ligand of Vibrio fischeri as L and D isomers[1].

[References]

[1]. Li SZ, et al. Influence of the d/l configuration of N-acyl-homoserine lactones (AHLs) and analogues on their Lux-R dependent quorum sensing activity. Bioorg Chem. 2018 Apr;77:215-222.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
482.9±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₅NO₄

[ Molecular Weight ]:
213.230

[ Flash Point ]:
245.9±28.7 °C

[ Exact Mass ]:
213.100113

[ PSA ]:
72.47000

[ LogP ]:
-1.17

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.486

[ Storage condition ]:
−20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Substrate specificity and function of the pheromone receptor AinR in Vibrio fischeri ES114.

J. Bacteriol. 195(22) , 5223-32, (2013)

Two distinct but interrelated pheromone-signaling systems, LuxI/LuxR and AinS/AinR, positively control bioluminescence in Vibrio fischeri. Although each system generates an acyl-homoserine lactone (AH...

Attenuation of Vibrio fischeri quorum sensing using rationally designed polymers.

Biomacromolecules 11(4) , 975-80, (2010)

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 desig...

The crystal structure of the Escherichia coli autoinducer-2 processing protein LsrF.

PLoS ONE 4(8) , e6820, (2009)

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 tr...

Related Compounds

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