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61698
N-(3-Hydroxyoctanoyl)-DL-homoserin-lacton
≥95% (sum of isomers, HPLC)
Synonym(e):
3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)-octanamid, 3-Hydroxy-C8-HSL, N-[(RS)-3-Hydroxyoctanoyl]-DL-homoserin-lacton
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About This Item
Empirische Formel (Hill-System):
C12H21NO4
CAS-Nummer:
Molekulargewicht:
243.30
MDL-Nummer:
UNSPSC-Code:
41116134
PubChem Substanz-ID:
NACRES:
NA.25
Empfohlene Produkte
Qualitätsniveau
Assay
≥95% (sum of isomers, HPLC)
Lagertemp.
−20°C
SMILES String
O=C(CC(O)CCCCC)NC1C(OCC1)=O
InChI
1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)
InChIKey
XCZVBYOXRSFQBH-UHFFFAOYSA-N
Biochem./physiol. Wirkung
N-(3-Hydroxyoctanoyl)-DL-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, cell to cell communication among bacteria; for reviews see. 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.
Lagerklassenschlüssel
11 - Combustible Solids
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
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Clay Fuqua et al.
Nature reviews. Molecular cell biology, 3(9), 685-695 (2002-09-05)
Bacterial cell-to-cell signalling has emerged as a new area in microbiology. Individual bacterial cells communicate with each other and co-ordinate group activities. Although a lot of detail is known about the mechanisms of a few well-characterized bacterial communication systems, other
Bonnie L Bassler
Cell, 109(4), 421-424 (2002-06-28)
In a process called quorum sensing, groups of bacteria communicate with one another to coordinate their behavior and function like a multicellular organism. A diverse array of secreted chemical signal molecules and signal detection apparatuses facilitate highly productive intra- and
Regulation of gene expression by cell-to-cell communication: acyl-homoserine lactone quorum sensing.
C Fuqua et al.
Annual review of genetics, 35, 439-468 (2001-11-09)
Quorum sensing is an example of community behavior prevalent among diverse bacterial species. The term "quorum sensing" describes the ability of a microorganism to perceive and respond to microbial population density, usually relying on the production and subsequent response to
Dilani Senadheera et al.
Advances in experimental medicine and biology, 631, 178-188 (2008-09-17)
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Margrith E Mattmann et al.
The Journal of organic chemistry, 75(20), 6737-6746 (2010-08-03)
Bacteria use small molecule signals to access their local population densities in a process called quorum sensing (QS). Once a threshold signal concentration is reached, and therefore a certain number of bacteria have assembled, bacteria use QS to change gene
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