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O9139

Sigma-Aldrich

N-(3-Oxododecanoyl)-L-homoserine lactone

≥98% (TLC)

Sinónimos:

3-Oxo-C12-HSL

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About This Item

Fórmula empírica (notación de Hill):
C16H27NO4
Número de CAS:
168982-69-2
Peso molecular:
297.39
MDL number:
MFCD08275140
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
329818935
NACRES:
NA.26

product name

N-(3-Oxododecanoyl)-L-homoserine lactone, quorum sensing signaling molecule

Quality Level

200

assay

≥98% (TLC)

form

powder

color

white

application(s)

cell analysis

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O

InChI

1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1

InChI key

PHSRRHGYXQCRPU-AWEZNQCLSA-N

Application

N-(3-Oxododecanoyl)-L-homoserine lactone (3-Oxo-C12-HSL), a member of a family of acyl homoserine lactones, may be used to determine its mechanisms and specificity of action as a signaling molecule involved in the regulation of bacterial quorum sensing.

Biochem/physiol Actions

N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL) is among a group of homoserine lactones that includes: N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
Acyl homoserine lactone that is an autoinducer of quorum sensing by Pseudomonas aeruginosa. Degraded by paraoxonase (PON) family members.

also commonly purchased with this product

Referencia del producto
Descripción
Precios

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Gene PA2449 Is Essential for Glycine Metabolism and Pyocyanin
Biosynthesis in Pseudomonas aeruginosa PAO1
Lundgren BR, et al.
Journal of Bacteriology, 195(9), 2087-2100 (2013)
Yang Yang et al.
Frontiers in microbiology, 9, 1924-1924 (2018-09-05)
Quorum sensing (QS) is a central mechanism for regulating bacterial social networks in biofilm via the production of diffusible signal molecules (autoinducers). In this work, we assess the contribution of QS autoinducers to microbial extracellular electron transfer (EET) by Pseudomonas
Nathaniel C Cady et al.
PloS one, 7(6), e38492-e38492 (2012-06-21)
Using a microplate-based screening assay, the effects on Pseudomonas aeruginosa PAO1 biofilm formation of several S-substituted cysteine sulfoxides and their corresponding disulfide derivatives were evaluated. From our library of compounds, S-phenyl-L-cysteine sulfoxide and its breakdown product, diphenyl disulfide, significantly reduced
Stephanie J Cole et al.
Nature communications, 9(1), 4436-4436 (2018-10-27)
Chronic bacterial infections on medical devices, including catheter-associated urinary tract infections (CAUTI), are associated with bacterial biofilm communities that are refractory to antibiotic therapy and resistant to host immunity. Previously, we have shown that Pseudomonas aeruginosa can cause CAUTI by
Lisheng Liao et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(29), 7587-7592 (2018-07-04)
Many species of Proteobacteria produce acyl-homoserine lactone (AHL) compounds as quorum-sensing (QS) signals for cell density-dependent gene regulation. Most known AHL synthases, LuxI-type enzymes, produce fatty AHLs, and the fatty acid moiety is derived from an acyl-acyl carrier protein (ACP)
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