74359
N-[(RS)-3-Hydroxybutyryl]-L-homoserine lactone
≥96% (HPLC)
Synonym(s):
3-Hydroxy-C4-HSL, N-(3-Hydroxybutanoyl)-L-homoserine lactone
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About This Item
Empirical Formula (Hill Notation):
C8H13NO4
CAS Number:
Molecular Weight:
187.19
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
assay
≥96% (HPLC)
form
powder
storage temp.
−20°C
SMILES string
CC(O)CC(=O)N[C@H]1CCOC1=O
InChI
1S/C8H13NO4/c1-5(10)4-7(11)9-6-2-3-13-8(6)12/h5-6,10H,2-4H2,1H3,(H,9,11)/t5?,6-/m0/s1
InChI key
FIXDIFPJOFIIEC-GDVGLLTNSA-N
Biochem/physiol Actions
N-[(RS)-3-Hydroxybutyryl]-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, cell to cell communication among bacteria; for reviews see[1][2][3][4][5]. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs[3], and a research focus for the prevention of biofilm formation[6][7][8].
Quorum-sensing signal generation
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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B L Hanzelka et al.
Journal of bacteriology, 181(18), 5766-5770 (1999-09-11)
Acylhomoserine lactones, which serve as quorum-sensing signals in gram-negative bacteria, are produced by members of the LuxI family of synthases. LuxI is a Vibrio fischeri enzyme that catalyzes the synthesis of N-(3-oxohexanoyl)-L-homoserine lactone from an acyl-acyl carrier protein and S-adenosylmethionine.
Sathish Rajamani et al.
Journal of microbiological methods, 84(2), 189-193 (2010-12-07)
Many bacteria produce and secrete proteases during host invasion and pathogenesis. Vibrio harveyi, an opportunistic pathogen of shrimp, is known to use a two-component quorum sensing (QS) mechanism for coordination of gene expression including protease secretion at high population densities.
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
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
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
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