68873
N-(3-Hydroxydecanoyl)-DL-homoserine lactone
Synonym(s):
3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)decanamide, N-[(RS)-3-Hydroxydecanoyl]-DL-homoserine lactone
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About This Item
Empirical Formula (Hill Notation):
C14H25NO4
CAS Number:
Molecular Weight:
271.35
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
41116134
MDL number:
InChI
1S/C14H25NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h11-12,16H,2-10H2,1H3,(H,15,17)
SMILES string
O=C(CC(O)CCCCCCC)NC1C(OCC1)=O
InChI key
DOICJCCMIBBSOO-UHFFFAOYSA-N
form
powder
storage temp.
−20°C
Quality Level
Biochem/physiol Actions
N-(3-Hydroxydecanoyl)-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.
Quorum-sensing signal generation
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_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
M B Miller et al.
Annual review of microbiology, 55, 165-199 (2001-09-07)
Quorum sensing is the regulation of gene expression in response to fluctuations in cell-population density. Quorum sensing bacteria produce and release chemical signal molecules called autoinducers that increase in concentration as a function of cell density. The detection of a
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
Jie Zhu et al.
Current opinion in pharmacology, 13(5), 688-698 (2013-07-24)
With the emergence of microbial pathogens increasingly resistant against commonly used antibiotics, new treatment strategies are desperately needed. Bacterial quorum sensing has attracted a lot of attention over the last decade as a potential new target for antimicrobial therapy. Interference
Dilani Senadheera et al.
Advances in experimental medicine and biology, 631, 178-188 (2008-09-17)
Streptococcus mutans is the primary causative agent involved in dental caries in humans. Among important virulence factors of this pathogen, its ability to form and sustain a polysaccharide-encased biofilm (commonly called dental plaque) is vital not only to its survival
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