H7890
L-Homoserine lactone hydrochloride
suitable for ligand binding assays
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About This Item
Empirical Formula (Hill Notation):
C4H7NO2 · HCl
CAS Number:
Molecular Weight:
137.56
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
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product name
L-Homoserine lactone hydrochloride,
form
powder
technique(s)
ligand binding assay: suitable
color
white
storage temp.
−20°C
SMILES string
Cl.N[C@H]1CCOC1=O
InChI
1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
InChI key
XBKCXPRYTLOQKS-DFWYDOINSA-N
General description
L-Homoserine lactone (HSL), also called acyl-HSL, comprises a homoserine lactone ring and a fatty acyl side. The levels of acyl-HSL in bacteria is dictated by the availability of the substrates and acyl-homoserine lactones synthase.
Application
L-Homoserine lactone hydrochloride has been used as an inhibitor for arterial smooth muscle contraction.
Biochem/physiol Actions
L-Homoserine lactone inhibition reduces virulence factors and halts inflammation and tissue damage. In Pseudomonas aeruginosa it controls virulence factor production and biofilm formation. In Agrobacterium tumefaciens, it is essential for conjugal transfer.
Acylated L-Homoserine lactone(s) are used to study bacterial quorum-sensing signaling mechanisms.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Inhibiting N-acyl-homoserine lactone synthesis and quenching Pseudomonas quinolone quorum sensing to attenuate virulence
Chan KG, et al.
Frontiers in Microbiology, 6, 1173-1173 (2015)
Nathan A Ahlgren et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(17), 7183-7188 (2011-04-08)
Many Proteobacteria possess LuxI-LuxR-type quorum-sensing systems that produce and detect fatty acyl-homoserine lactone (HSL) signals. The photoheterotroph Rhodopseudomonas palustris is unusual in that it produces and detects an aryl-HSL, p-coumaroyl-HSL, and signal production requires an exogenous source of p-coumarate. A
Long-chain acyl-homoserine lactone quorum-sensing regulation of Rhodobacter capsulatus gene transfer agent production
Schaefer AL, et al.
Journal of Bacteriology, 184(23), 6515-6521 (2002)
Defining the structure and function of acyl-homoserine lactone autoinducers
Churchill MEA, et al.
Methods in Molecular Biology, 692(23), 159-171 (2011)
The Pseudomonas aeruginosa quorum-sensing signal molecule, N-(3-oxododecanoyl)-l-homoserine lactone, inhibits porcine arterial smooth muscle contraction
Lawrence RN, et al.
British Journal of Pharmacology, 128(4), 845-848 (1999)
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