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Merck

44558

Sigma-Aldrich

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

別名:

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide, C8-HSL

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About This Item

実験式(ヒル表記法):
C12H21NO3
CAS番号:
分子量:
227.30
Beilstein:
8148282
MDL番号:
UNSPSCコード:
12352211
PubChem Substance ID:
NACRES:
NA.85

製品名

N-Octanoyl-L-homoserine lactone, ≥96% (HPLC)

品質水準

アッセイ

≥96% (HPLC)

フォーム

powder or crystals

光学活性

[α]/D -28±3°, c = 0.2 in methanol

white to off-white

適合性

conforms to structure for Proton NMR spectrum

アプリケーション

detection

保管温度

−20°C

SMILES記法

O=C1OCC[C@@H]1NC(CCCCCCC)=O

InChI

1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1

InChI Key

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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生物化学的/生理学的作用

N-Octanoyl-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, colonization, chemical defense and cell to cell communication among bacteria; for reviews see. AHLs are released as oligopeptides in Gram positive bacteria and as quorum signal in Gram negative bacteria. 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.
Quorum-sensing signal generation

保管分類コード

11 - Combustible Solids

WGK

WGK 3

引火点(°F)

Not applicable

引火点(℃)

Not applicable


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J B Andersen et al.
Applied and environmental microbiology, 67(2), 575-585 (2001-02-07)
In order to perform single-cell analysis and online studies of N-acyl homoserine lactone (AHL)-mediated communication among bacteria, components of the Vibrio fischeri quorum sensor encoded by luxR-P(luxI) have been fused to modified versions of gfpmut3* genes encoding unstable green fluorescent
Mattia Marenda et al.
Scientific reports, 6, 39142-39142 (2016-12-15)
Bacterial communities undergo collective behavioural switches upon producing and sensing diffusible signal molecules; a mechanism referred to as Quorum Sensing (QS). Exemplarily, biofilm organic matrices are built concertedly by bacteria in several environments. QS scope in bacterial ecology has been
A Kuo et al.
Journal of bacteriology, 178(4), 971-976 (1996-02-01)
Population density-dependent expression of luminescence in Vibrio fischeri is controlled by the autoinducer N-3-oxohexanoyl-L-homoserine lactone (autoinducer 1 [AI-1]), which via LuxR activates transcription of the lux operon (luxICDABEG, encoding the putative autoinducer synthase [LuxI] and the luminescence enzymes). We recently
Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
José Gomes et al.
Chemical communications (Cambridge, England), 49(2), 155-157 (2012-11-22)
We demonstrate the synthesis and immobilization of natural product hybrids featuring an acyl-homoserine lactone and a nitrodopamine onto biocompatible TiO(2) surfaces through an operationally simple dip-and-rinse procedure. The resulting immobilized hybrids were shown to be powerful quorum sensing (QS) activators

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