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
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. 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
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class Code
13 - Non Combustible Solids
WGK
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.
Barbara Thallinger et al.
Biotechnology journal, 8(1), 97-109 (2013-01-03)
With the increasing prevalence of antibiotic resistance, antimicrobial enzymes aimed at the disruption of bacterial cellular machinery and biofilm formation are under intense investigation. Several enzyme-based products have already been commercialized for application in the healthcare, food and biomedical industries.
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
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
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